Crystal structure of bis(cyclohexylammonium) diphenyldioxalatostannate(IV)

In the title salt, (CyNH3)2[Sn(Ph2)(C2O4)2] (Cy is cyclo­hexyl and Ph is phen­yl), the SnPh2 moiety is chelated by two oxalate anions, leading to a cis arrangement within the distorted octa­hedral coordination sphere of the SnIV atom.

Organotin(IV) trifluoromethanesulfonates chemistry: Isolation and characterization of a new di-n-butyl derivative presenting a Sn3O3 core

Abstract Reaction of the dimeric hydroxo di-n-butylstannane trifluoromethanesulfonato complex [n-Bu2Sn(OH)(H2O)(CF3SO3)]2 (1) with a mixture of anthracene (C14H10, Ant) and phenazine (C12H8N2, Phz) in dichloromethane at room temperature yielded the novel di-n-butyltin(IV) trifluoromethanesulfonate salt {[n-Bu2Sn(H2O)]2O·n-Bu2Sn(OH)2}(CF3SO3)2 (2), together with the co-crystallization of phenazinium trifluoromethanesulfonate salts ([C12H9N2][CF3SO3], PhzH) collected in the solid state in two distinct self-assembled architectures, 3 and 4, showing π–π stacking interactions, and involving the intercalation of free molecules of phenazine and anthracene, respectively. Complex 2 is a cationic tri…

Palladium-catalyzed formation of secondary and tertiary amines from aryl dihalides with air-stable ferrocenyl tri- and diphosphines: Synthesis and X-ray structure of efficient catalysts beyond [PdCl2(DPPF)]

Abstract Robust, air-stable tridentate and bidentate ferrocenylphosphines 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene, L5, and 1,1′-bis(diisopropylphosphino)-3,3′-bis(tert-butyl)ferrocene, L9, combined with 1 mol% of [PdCl(η3-C3H5)]2 led to two new catalytic systems which allow the coupling of aniline derivatives with mono- and dihaloarenes to form functionalized diarylamines and triarylamines. The excellent selectivity of the reactions avoids the deleterious dehalogenation of the substrates and products. The X-ray structure characterization of the related complex [PdCl2(L9)] is reported in which ligand L9 in its meso form is significantly distorted.

Diastereoselective Synthesis of Dialkylated Bis(phosphino)ferrocenes: Their Use in Promoting Silver-Mediated Nucleophilic Fluorination of Chloroquinolines

International audience; The diastereoselective synthesis of dialkylated ferrocenyl bis(phosphane)s bearing aryl, alkyl, and hetero- or polycyclic substituents on the phosphino groups is reported, together with their characterization in the solid state by X-ray structure analysis and in solution by multinuclear NMR spectroscopy. Introduction of various alkyl groups on the ferrocene backbone, namely, tert-butyl, isopropyl, and trimethylsilyl, has a significant influence on the stereoselectivity of the ensuing lithiation/phosphination reactions. Only the introduction of the tert-butyl groups ensures both a high yield and perfect diastereoselectivity, which leads to the exclusive formation of t…

Direct arylation of heteroaromatic compounds with congested, functionalised aryl bromides at low palladium/triphosphane catalyst loading.

International audience; A new ferrocenyl triphosphane ligand associated to palladium was found to be an efficient catalyst for the direct coupling of highly congested, functionalised aryl bromides with a variety of heteroarenes. These coupling reactions can generally be performed by using a low-loading (0.1-0.5 mol%) of the catalyst. The present protocol tolerates important and useful functional groups, which allows for further elaboration into more sophisticated heterocyclic molecules. The straightforward arylation of heteroaromatic compounds with congested ortho-substituted aryl bromides may permit further convergent syntheses of diverse ligands, biologically active molecules and molecula…

Palladium-catalyzed heteroaryl thioethers synthesis overcoming palladium dithiolate resting states inertness: Practical road to sulfones and NH-sulfoximines

International audience; We provide efficient synthetic access to heteroaryl sulfones in two-steps using a simple palladium-1,1'-bis [(diphenyl)phosphanyl]ferrocene catalyst to form in high yields variously functionalized heteroaromatic thioethers. Pyridinyl-containing substrates can be subsequently selectively oxidized into sulfones and NH-sulfoximines by using very mild oxidation conditions with a high functional group tolerance. In the palladium catalyzed C-S coupling of heteroaromatic thiols, reactivity limitation is attached with electron-deficient thiols. We show that this limitation can be resolved by the successful use of 2-bromoheteroarenes in the C-S coupling. We established herein…

(2-Pyridyl)sulfonyl Groups for ortho -Directing Palladium- Catalyzed Carbon-Halogen Bond Formation at Functionalized Arenes

International audience; We describe an efficient palladium-catalyzed selective C-H ortho-monohalogenation (X=I, Br, Cl, F) of various functionalized (2-pyridyl) aryl-sulfones. ortho-, meta-and para-functionalization is tolerated at the arene group which undergoes C-H halogenation. Some modifications are also possible on the 2-(arylsulfonyl) heteroaryl directing groups. A comparison of the halogenation efficiency suggests that bromination is the practical method of choice, while chlorination and fluorination are possible but more challenging. Under forcing conditions ortho-dihalogenation can also be achieved.

Electrosynthesis and X‐ray Crystallographic Structure of Zn II meso ‐Triaryltriphenylphosphonium Porphyrin and Structural Comparison with Mg II meso ‐Triphenylphosphonium Porphine

Functionalized Tri‐ and Tetraphosphine Ligands as a General Approach for Controlled Implantation of Phosphorus Donors with a High Local Density in Immobilized Molecular Catalysts

Supported phosphine ligands are auxiliaries of topical academic and industrial interest in catalysis promoted by transition metals. However, both controlled implantation and controlled conformation of ligands should be achieved to produce immobilized catalysts that are able to structurally “copy” efficient homogeneous systems. We provide herein a general synthetic strategy for assembling a new class of branched tetra- and triphosphine ligands with a unique controlled rigid conformation, and thus providing a high local density of phosphorus atoms for extended coordination to the metal center. We prepared new functionalized cyclopentadienyl (Cp) salts to design polyphosphines that were “ready…

Tribenzylammonium chloride

Single crystals of the title salt, C21H21NH+·Cl−, were isolated as a side product from the reaction involving [(C6H5CH2)3NH]2[HPO4] and Sn(CH3)3Cl in ethanol. Both the cation and the anion are situated on a threefold rotation axis. The central N atom in the cation has a slightly distorted tetrahedral environment, with angles ranging from 107.7 to 111.16 (10)°. In the crystal, the tribenzylammonium cations and chloride anions are linked through N—H...Cl and C—H...Cl hydrogen bonds, leading to the formation of infinite chains along [001]. The crystal studied was a merohedral twin.

Propane-1,3-diammonium molybdate

The reaction between equimolar amounts of propane-1,3-diamine and molybdenum trioxide in water led to the formation of single crystals of the title salt, (C3H12N2)[MoO4]. The asymmetric unit is comprised of one propane-1,3-diammonium cation and one molybdate anion. The latter is isolated in the structure and has a slightly distorted tetrahedral configuration. An extensive network of N—H...O hydrogen bonds connects anions and cations, giving rise to a compact three-dimensional packing.

Crystal structure of 2-methyl-1H-imidazol-3-ium hydrogen oxalate dihydrate

In the title mol­ecular salt 2-methyl-1H-imidazol-3-ium hydrogen oxalate dihydrate, N—H⋯(O,O) and O—H⋯O hydrogen bonds link the components into a bilayer-like assembly.

Synthesis, spectroscopic study, and crystal structure of a new organotin(IV) selenate derivative

Abstract The polymeric organotin(IV) selenate complex [(Me3Sn)3(SeO4)(OH)]n (1) has been isolated as single crystals from the reaction of [(Me2NH2)2SeO4] and Me3SnCl in methanol. In the solid state, compound 1 was characterized by X-ray diffraction analysis, Fourier transform-infrared spectroscopy, and elemental analysis. 1 crystallizes in the orthorhombic system space group Pbca with a=11.0231(2) Å, b=16.3461(3) Å, c=20.9945(4) Å, α=β=γ=90°, V=3782.89(12) Å3, and Z=8. Its structure can be described as a polymeric zigzag chain based on Me3Sn moieties linked by tridentate selenate anions. Pendant (Me3Sn)2OH groups are also connected to the chain, according to a syndiotactic organization, and…

Highly Functionalized Ferrocenes

International audience; Ferrocene is unique among organometallic compounds, and serves notably as a versatile platform towards the production of ligands useful to promote transition metals chemistry. A general limiting aspect of the synthesis of ferrocene derivatives is the efficient access to sophisticated highly functionalized polysubstituted ferrocenes, i. e. bearing four or more substituents replacing hydrogen atoms on the cyclopentadienyl rings. These ferrocene derivatives can bear various functional or/and structuring spectator substituents. Their preparation involves synthetic difficulties resulting from the need of multiple functionalizations coexisting altogether, and satisfying fu…

"Through-space" 31P spin-spin couplings in ferrocenyl tetraphosphine coordination complexes: improvement in the determination of the distance dependence of J(P,P) constants

Abstract From the analysis of several nickel and palladium halide complexes of a constrained ferrocenyl tetraphosphine, the existence in solution phase of unique 31P–31P “through-space” nuclear spin–spin coupling constants (JPP) had been previously evidenced. Due to the blocked conformation of the species in solution, and based on the NMR spectra obtained for the complexes and their corresponding solid state X-ray structures, these JPP constants had been shown to clearly depend on the mutual spatial position of the corresponding phosphorus atoms. Herein, the quantitative correlation disclosed at that time (P⋯P distance dependence of coupling constants) is remarkably confirmed, and mathemati…

First Annelated Azaphosphole-Ferrocenes: Synthetic Pathways and Structures

The first annelated bis- and mono-3H-1,3-azaphosphole ferrocene sandwich compounds have been synthesized from aminoferrocenes, and their X-ray structures are compared to those of their selenide-protected P═Se analogues, showing net discrepancies both in metallocene backbone conformation and in fused-ring planarity.

ChemInform Abstract: Electrosynthesis of Imidazolium Carboxylates.

For the first time the synthesis of imidazolium carboxylates is efficiently achieved by electrochemical reduction of imidazolium salts under very mild conditions.

Synthesis and characterization of novel quinolyl porphyrins as receptors. Study of their association with halophenols and 4nitrophenol as a reference

International audience; In this work, new receptors built on the porphyrin scaffold were synthesized for halophenols recognition. A quinolyl group was introduced on the porphyrin's periphery as binding site, to form two series of molecules based on two distinct porphyrin frames and which were obtained in free base and zinc forms. The binding between these porphyrin based receptors and halophenols (2,3,4,6tetrachlorophenol, 2,4,6-trichlorophenol or 2,4,6-tribromophenol) was studied. As established by 1 H NMR spectroscopy, the binding constants are in the range of two-digit numbers, which value is correlated with the porphyrin structure (substitutive pattern, form of the free base or Zn II co…

Bis(cyclohexylammonium) tetrachlorido(oxalato)stannate(IV)

The title salt, (C6H14N)2[Sn(C2O4)Cl4], was obtained as a by-product from the reaction between 2C6H14N+·C2O42−·1.5H2O and SnCl2·2H2O. The cyclohexylammonium cation has a chair conformation. The complex anion consists of an oxalate anion chelating the SnCl4 moiety, resulting in a distorted octahedral coordination sphere of the SnIV atom with the O atoms in equatorial cis positions. In the crystal, cations and anions are linked through N—H...O and N—H...Cl interactions into a layered arrangement parallel to (100).

Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines

International audience; Direct unequal C-H bond difunctionalization of phosphorylated diamantane was achieved in high yield from the corresponding phosphonates. Reduction of the functionalized phosphonates provides access to novel primary and secondary alkyl/aryl diamantane phosphines. The prepared primary diamantyl phosphines are quite air stable compared to their adamantyl and especially alkyl or aryl analogues. This finding is corroborated by comparing the singly occupied molecular orbital energy levels of the corresponding phosphine radical cations obtained by density functional theory computations.

Electrosynthesis of imidazolium carboxylates.

Synthesis of imidazolium carboxylate compounds was efficiently achieved by electrochemical reduction of imidazolium precursors under very mild conditions.

Crystallographic, spectroscopic and electrochemical characterization of pyridine adducts of magnesium(II) and zinc(II) porphine complexes

Abstract A new purification method of magnesium(II) and zinc(II) porphine complexes (MgP and ZnP, respectively) by crystallization of their respective pyridine adducts is described. Pure MgP and ZnP can be regenerated by removal of the coordinated pyridine ligands by heating at 200 °C under vacuum. X-ray crystallographic structures of the pyridine adducts are presented for the first time. NMR analyses of the adducts reveal the coordination of two pyridine molecules. Electrochemical as well as UV-vis absorption spectroscopy analyses in DMF of MgP·(Py)2, ZnP·(Py)2, MgP and ZnP indicate that pyridine adducts are totally dissociated. Besides, oxidation peaks of these complexes are totally irrev…

Control over the oxidative reactivity of metalloporphyrins. Efficient electrosynthesis of meso,meso-linked zinc porphyrin dimer.

The electrochemical oxidation of zinc(II) 5,15-p-ditolyl-10-phenylporphyrin at its first oxidation potential leads to the formation of the corresponding meso-meso porphyrin dimer as the main product. The number of electrons abstracted, the addition of the hindered base 2,6-lutidine as well as operating in DMF, instead of a CH(2)Cl(2)/CH(3)CN mixture are the key parameters to obtain high yields of the desired coupling product. Indeed, when the electrolyses are carried out in the CH(2)Cl(2)/CH(3)CN mixture, the unexpected zinc(II) 5-chloro-10,20-p-ditolyl-15-phenyl porphyrin is produced as a by-product, the chlorine atom originating from the CH(2)Cl(2) solvent. The monomer and the dimer are c…

Aromatic Nucleophilic Substitution (SNAr) of meso-Nitroporphyrin with Azide and Amines as an Alternative Metal Catalyst Free Synthetic Approach To Obtain meso-N-Substituted Porphyrins

International audience; Aromatic nucleophilic substitution reaction of the nitro group of meso-nitroporphyrins with azide and various amines was achieved and represents an alternative procedure to C-N coupling reactions usually needed to obtain such meso-N-substituted porphyrins in good yields.

Crystal structure of the bis(cyclohexylammonium) succinate succinic acid salt adduct

The title salt adduct comprises two cyclo­hexyl­ammonium cations, one succinate anion and one mol­ecule of succinic acid, linked together through inter­molecular hydrogen-bonding inter­actions giving a two-dimensional layer-like self-assembly lying parallel to (010).

Gold-Catalyzed Suzuki Coupling of ortho -Substituted Hindered Aryl Substrates

International audience; A method that allows hindered ortho-substituted aryl iodides to be efficiently coupled to phenylboronic acid using a gold-catalyzed C-C bond formation is presented. The use of a molecularly-defined dinuclear gold chloride catalytic precursor that is stabilized by a new tetradentate (N,N')-diamino-(P,P')-diphosphino ferrocene hybrid ligand in a Suzuki-type reaction is described for the first time. Electron-rich isopropyl groups on phosphorus were found essen-tial for a superior activity, while the performances of a set of analogous gold dinuclear complexes that were fully characterized by multinuclear NMR spectroscopy and XRD analysis, were investigated. Therefore, ar…

Electron‐Sponge Behavior, Reactivity and Electronic Structures of Cobalt‐Centered Cubic Co 9 Te 6 (CO) 8 Clusters (Eur. J. Inorg. Chem. 12/2008)

The cover picture shows an organometallic electron sponge and an elephant-ear sponge in the background (photo by F. and J. Burek, National Marine Sanctuaries). The electronic flexibility of the cobalt-centered cubic [Co9Te6(CO)8]n cluster ([3]n) in the central circle is expressed by differently charged states (n = 1+ to 5–). Starting from the upper left corner of our graphic in a clockwise direction, neutral [Co9Te6(CO)4(PPh3)4], structurally diverse networks of [Ph3PNPPh3][3] and [Ph3PNPPh3]2[3] salts and the core of the [Co9Te3{ν5-Cp′2Nb(CO)Te}3(CO)8] cluster as a pseudo-protonated representative of the [3]3– anion are shown. Details of the structural, electrochemical and theoretical prop…

Selective Preparation of Diamondoid Phosphonates

We present an effective sequence for the preparation of phosphonic acid derivatives of the diamondoids diamantane, triamantane, [121]tetramantane, and [1(2,3)4]pentamantane. The reactions of the corresponding diamondoid hydroxy derivatives with PCl3 in sulfuric or trifluoroacetic acid give mono- as well as didichlorophosphorylated diamondoids in high preparative yields.

Electrosynthesis of Poly(alanine)-Like Peptides in Concentrated Alanine Based Electrolytes, Characterization Coupled to DFT Study and Application to pH Proton Receptor

The anodic oxidation of concentrated l-alanine on smooth electrodes such as platinum and glassy carbon electrodes was studied. Contrary to the previous studies performed up to now with diluted l-alanine, the electrochemical process generated here results in a completely different situation. The oxidation on smooth platinum was carried out by electrochemical quartz crystal microbalance (EQCM) coupled to cyclic voltammetry technique. The effects of concentration, scan rate, and pH (zwitterion at pH = 6 and alkaline media at pH = 13) on potential values were examined. Glassy carbon and smooth gold electrodes showed the same behavior as on smooth platinum electrode. Spectroscopic analysis such …

Tris(cyclo-hexyl-ammonium) cis-di-chlorido-bis-(oxalato-κ(2) O (1),O (2))stann-ate(IV) chloride monohydrate.

The crystal structure of the title compound, (C6H14N)3[Sn(C2O4)2Cl2]Cl·H2O, contains three cyclohexylammonium cations, one stannate(IV) dianion, one isolated chloride anion and one lattice water molecule. The cyclohexylammonium cations adopt chair conformations. In the complex anion, two bidentate oxalate ligands and two chloride anions incispositions coordinate octahedrally to the central SnIVatom. The cohesion of the molecular entities is ensured by the formation of N—H...O, O—H...O, O—H...Cl and N—H...Cl interactions involving cations, anions and the lattice water molecule, giving rise to a layer-like arrangement parallel to (010).

Kinetic and Electrochemical Studies of the Oxidative Addition of Demanding Organic Halides to Pd(0): the Efficiency of Polyphosphane Ligands in Low Palladium Loading Cross-Couplings Decrypted

International audience; Oxidative addition (OA) of organic halides to palladium(0) species is a fundamental reaction step which initiates the C–C bond formation catalytic processes typical of Pd(0)/Pd(II) chemistry. The use of structurally congested polyphosphane ligands in palladium-catalyzed C–C bond formation has generated very high turnover numbers (TONs) in topical reactions such as Heck, Suzuki, Sonogashira couplings, and direct sp2C–H functionalization. Herein, the OA of aryl bromides to Pd(0) complexes stabilized by ferrocenylpolyphosphane ligands L1 (tetraphosphane), L2 (triphosphane), and L3 (diphosphane) is considered. The investigation of kinetic constants for the addition of Ph…

Linear Triphosphines as Ligands for Metal Complexes Immobilization in Ionic Liquids: Palladium-Catalyzed Methoxylation of Alkynes

Several novel palladium triphosphine complexes have been synthesized and tested as recyclable catalysts for the methoxylation of alkynes into acetals in ionic liquids. A complete conversion of phenylacetylene was achieved with only 0.2% of (Pd(Triphos)NCMe)((PF6)2) in a methanol/(BMIM)(BF4) mixture. We discovered that the addition of an ionic liquid to methanol allowed not only to increase the activity of the palladium catalyst but also to provide a recyclable catalyst which can be reused several times with a weaker drop of activity. To complete these catalytic studies, we describe the synthesis of the first poor -electron-donating/strong -electron-acceptor linear Triphosphine which, afte…

Gold(I) Complexes Nuclearity in Constrained Ferrocenyl Diphosphines: Dramatic Effect in Gold‐Catalyzed Enyne Cycloisomerization

International audience; Di-tert-butylated-bis(phosphino)ferrocene ligands bearing phosphino substituents R (R=phenyl, cyclohexyl, isopropyl, mesityl, or furyl) allow tuning the selective formation of Au(I) halide complexes. Thus, dinuclear linear twocoordinate, but also rare mononuclear trigonal three-coordinate and tetrahedral four-coordinate complexes were formed upon tuning of the conditions. Both Au(I) chloride and rarer Au(I) iodide complexes were synthesized, and their X-ray diffraction analysis are reported. The significance of the control of structure and nuclearity in Au(I) complexes is further illustrated herein by its strong effect on the efficiency and selectivity of gold-cataly…

Planar-Chiral 1,1 '-Diboryl Metallocenes: Diastereoselective Synthesis from Boryl Cyclopentadienides and Spin Density Analysis of a Diborylcobaltocene

International audience; The reaction of nonsubstituted alkali metal cyclopentadienides with haloboranes leads to similar to 90:10 mixtures of isomeric diene products that can be deprotonated to give simple boryl cyclopentadienides. We extended this transformation to the sterically hindered lithium tert-butylcyclopentadienide 1 using FBMe(s)2 (Mes = 2,4,6-trimethylphenyl) and ClBCy2 as electrophiles. The boryl group is selectively introduced in the remote position to minimize steric congestion. The new boryl dienes are obtained as mixtures of isomers, and subsequent deprotonation with MeLi or LiHMDS affords the lithium 1,3-disubstituted cyclopentadienides Sa,b in yields over 95%. Direct asse…

Unprecedented Hexa- and Undecanuclear Frameworks of Two New Tin(IV) Oxo Clusters Resulting from Partial Debenzylation Reactions

A new and facile synthetic route to the known neutral cluster ((PhCH2)2SnO)6[((PhCH2)2SnOH)2- (CO3)]2 (2) as well as its reactivity toward trifluoromethanesulfonic acid (HO3SCF3, TfOH) are reported. The solid-state structure of the new solvate 2·6C7H8 has been determined by single-crystal X-ray diffraction. The core of 2 can be described as a pair of coplanar pentanuclear [(PhCH2)2SnO]5 ladders bridged at their ends by two carbonate groups. Successive additions of TfOH to a suspension of 2 in CD3CN were monitored by 119Sn{1H} NMR spectroscopy showing the transformation of the fingerprint of 2 (δ = −244, −246, −306 ppm), via new upfield signals, to a final broad resonance located at δ = −474…

Evidence of intramolecular electron transfer between two metallic atoms in a bimetallic complex by electrochemical methods

The electrochemical properties of the monomeric complex [(η5-C5H5)(μ-η5:η1-C5H4(CH2)2P(C6H5)2TiCl2] 1 and the heterobimetallic complex [(η5-C5H5)(μ-η5:η1-C5H4(CH2)2P(C6H5)2TiCl2][RuCl2(C6H4(CH3)(C3H7))] 2 have been studied by cyclic voltammetry, controlled potential electrolysis and rotating disk electrode voltammetry. An unexpected electron transfer between the two heterobimetallic atoms has been observed. This transfer takes place via an intramolecular interaction, hence via a chloride bridge. Electrochemical simulation has been carried out to verify experimental results and to obtain the kinetic constant of the proposed square scheme.

Direct Writing on Copper Ion Doped Silica Films by Electrogeneration of Metallic Microstructures

International audience; A facile and rapid localized electrochemical reduction of colloid copper particles is proposed using the scanning electrochemical,microscope (SECM), technique. In this purpose, thin films of composite silica :glass containing copper salts were prepared by the sol-gel method via the dip coating technique. Acid-catalyzed tetraethylorthosilane (TEOS) solutions charged with copper nitrate were used as precursors. This one-pot experiment can be performed in mild conditions. The localized generation of copper metallic nanostructures on silica film has been performed by electroreduction of methyl viologen on an ultramicroelectrode (UME). The UME generates reducing species, …

Experimental and theoretical studies on electropolymerization of polar amino acids on platinum electrode

International audience; The anodic oxidation of polar amino acids (L-serine, L-threonine, L-asparagine, and L-glutamine) in aqueous electrolyte on smooth platinum electrode was carried out by cyclic voltammetry coupled to electrochemical quartz crystal microbalance (EQCM). pH (zwitterion, acidic and alkaline) effects on their electrochemical behavior were examined. The maximum current values are measured for zwitterion species. In addition, the current increases with increasing of concentration and scan rate, and decreases with increasing pH. The resulting passivation was studied by spectroscopic analysis such as attenuated total reflection FT infrared spectroscopy (ATR-FTIR), X-ray photoel…

s-Block metal scorpionates – A new sodium hydrido-tris(3,5-dimethyl-1-pyrazolyl)borate salt showing an unusual core stabilized by bridging and terminal O-bonded DMSO ligands

Abstract Dissolution of [(μ-Me2CO)3(NaTp*)2] (1) (Tp* = hydrido-tris(3,5-dimethyl-1-pyrazolyl)borate) in DMSO at room temperature leads to the growth of colourless crystals characterized as the new salt [Na2Tp*(μ-Me2SO)3(Me2SO)3] [NaTp* 2] (2). 2 crystallized in the trigonal space group R3 with Z = 3, a = 14.1227(2) Å, b = 14.1227(10) Å, c = 33.9685(2) Å, and V = 5867.35(17) Å3. Interestingly, anion and cation of 2 both contain the Tp* ligand. Moreover, the cationic moiety highlights an unusual sodium atom hexacoordinated by six DMSO molecules acting as O-bonded ligands. Three of which exhibit a bridging coordination mode and three are in terminal position. To the best of our knowledge, the…

Phosphasalen group IV metal complexes: synthesis, characterization and ring opening polymerization of lactide.

International audience; We report the synthesis of a series of Zr and Ti complexes bearing phosphasalen which differs from salen by the incorporation of two P atoms in the ligand backbone. The reaction of phosphasalen proligands (1a-1c)H2 with Zr(CH2Ph)4 led to different products depending on the nature of the N,N-linker in the ligand. In case of ethylene-linked phosphasalen, octahedral Zr complex 2a formed as a single stereoisomer in trans geometry. With the phenylene linker, it was shown by dynamic NMR spectroscopy that complex 2b exists as a mixture of trans and cis-β isomers in solution, both enantiomers (Δ and Λ) of the cis-β isomer being in fast equilibrium with respect to the NMR tim…

Phenoxyamidine Zn and Al Complexes: Synthesis, Characterization, and Use in the Ring-Opening Polymerization of Lactide

International audience; Herein we report the synthesis of new ditopic ligands, which consist of a phenoxy group and N,N,N'trisubstituted amidines linked by a methylene spacer (L1-L4). Their coordination chemistry has been studied/investigated with Zn(II) and Al(III). Alkane elimination route between the phenol-amidine proligands (L1H-L4H) and Et2Zn led to dinuclear complexes [(L1-L4)ZnEt]2 (1a-4a) in which the Zn centers are chelated by phenoxyamidine ligands and bridged through the oxygen atom of the phenoxy groups. Salt metathesis reaction between two equivalents of the sodium amidine phenate L1Na and ZnCl2 led to a bis-chelate chiral spiro-complex (L12Zn) 1a'. Analogous alkane eliminatio…

P-Chirogenic Phosphines Supported by Calix[4]arene: New Insight into Palladium-Catalyzed Asymmetric Allylic Substitution

The first P-chirogenic mono- and diphosphine ligands supported on the upper rim of a calix[4]arene moiety were synthesized using the ephedrine methodology. The lithiated calix[4]arene mono- and dianions both react with the oxazaphospholidine–borane, prepared from ephedrine, to afford regio- and stereoselectively the corresponding calix[4]arenyl aminophosphine–boranes, by cleavage of the heterocyclic ring at the P–O bond position. Subsequent reactions with HCl and then organolithium reagent and finally decomplexation with DABCO lead to the corresponding calix[4]arenyl mono- or diphosphines. Both enantiomers of the calix[4]arenyl phosphines were obtained either by using (+)- or (−)-ephedrine …

Coordinatively Unsaturated Amidotitanocene Cations with Inverted σ and π Bond Strengths: Controlled Release of Aminyl Radicals and Hydrogenation/Dehydrogenation Catalysis

Cationic amidotitanocene complexes [Cp2 Ti(NPhAr)][B(C6 F5 )4 ] (Cp=η5 -C5 H5 ; Ar=phenyl (1 a), p-tolyl (1 b), p-anisyl (1 c)) were isolated. The bonding situation was studied by DFT (Density Functional Theory) using EDA-NOCV (Energy Decomposition Analysis with Natural Orbitals for Chemical Valence). The polar Ti-N bond in 1 a-c features an unusual inversion of σ and π bond strengths responsible for the balance between stability and reactivity in these coordinatively unsaturated species. In solution, 1 a-c undergo photolytic Ti-N cleavage to release Ti(III) species and aminyl radicals ⋅NPhAr. Reaction of 1 b with H3 BNHMe2 results in fast homolytic Ti-N cleavage to give [Cp2 Ti(H3 BNHMe2 )…

Self-assembly through non-coordinating intermolecular forces, part 2 [1]. Synthesis, crystal structure and packing of [Cu2(μ-phthalazine) 3(phthalazine)2][CF3SO3]2

Abstract Treatment of the copper(I) trifluoromethanesulphonate toluene complex {[Cu(CF3SO3)]2 · C6H5Me} (1) with phthalazine (phtz, C8H6N2) in dichloromethane-acetonitrile solution yielded, via the bis(acetonitrile)tris(μ-phthalazine)dicopper(I) trifluoromethanesulphonate intermediate (2), the novel bis(phthalazine)tris(μ-phthalazine)dicopper(I) trifluoromethanesulphonate salt (3). Compound 3 was completely characterised and the molecular structure determined by single-crystal X-ray diffraction. Complex 3 crystallises in the monoclinic system, space group C2/c, with a = 26.9527(10), b = 10.9558(7), c = 19.2104(10) Å , β = 127.268(2)◦, V = 4514.3(4) Å3 and Z = 4. The copper(I) coordination g…

Copper(I) Iodide Polyphosphine Adducts at Low Loading for Sonogashira Alkynylation of Demanding Halide Substrates: Ligand Exchange Study between Copper and Palladium

The prestabilization of copper iodide with a multidentate ferrocenyl phosphine ligand promotes the palladium-catalyzed cross-coupling of demanding halides with phenylacetylene in a selective way. Novel CuI-triphosphine adducts are described in the solid state and in solution. Their use allowed the introduction of the copper iodide cocatalyst in unprecedented low amounts (0.4 to 0.1 mol %) in systems also employing low amounts of “ligand-free” [PdII(η3-allyl)Cl]2 precursor (0.2 to 0.05 mol %). The scope of substrates is reported, and electronically or sterically deactivated bromides were efficiently coupled. Concerning aryl chlorides, electron-poor activated substrates were also coupled usin…

New acridinium trifluoromethanesulfonate stacks induced in the presence of organotin(IV) complexes

Abstract Three new crystalline architectures based on acridinium trifluoromethanesulfonate salts [C13H10N]+[CF3SO3]– have been isolated as single crystals from the reaction of the dimeric hydroxo di-n-butylstannane trifluoromethanesulfonato complex [n-Bu2Sn(OH)(H2O)(CF3SO3)]2 (1) with acridine (C13H9N, Acr), in dichloromethane at room temperature. When an equimolar mixture of anthracene (C14H10, Ant) and acridine is initially used, the crystallization of a sandwich-type arrangement occurs, leading to the intercalation of one molecule of anthracene between two acridium trifluoromethanesulfonate salt molecules. In the three X-ray structures reported, the crystal packing involves the contribut…

Versatile redox reactivity of triaryl-meso-substituted Ni(ii) porphyrin

The electrochemical oxidation of nickel(II) 5,15-p-ditolyl-10-phenylporphyrin (1-Ni) leads to the formation of different coupling products, with the distribution depending on the nature of the solvent (CH2Cl2–CH3CN, CH2Cl2, DMF), the cell configuration (2 or 3 compartments) and the number of electrons abstracted. In a two compartment configuration (anode and cathode in the same compartment) in a CH2Cl2–CH3CN mixture, nickel(II) 5-chloro-10,20-p-ditolyl-15-phenylporphyrin (1-Ni-Cl) was isolated in good yield and its mechanism of formation is proposed. Switching to the three compartment configuration, the meso-β/meso-β doubly fused dimer (3-Ni) is detected as the major product whereas in pure…

ChemInform Abstract: Syntheses of Polyfunctionalized Resveratrol Derivatives Using Wittig and Heck Protocols.

In the modified Wittig reaction, Tms is used as a highly valuable protecting group of the phenolic functions of the starting arenes.

Electrochemical deposition of a luminescent alkoxysilyl-based fluorenone film exhibiting halide sensitivity

International audience

Synthesis of new cationic donor-stabilized phosphenium adducts and their unexpected P-substituent exchange reactions

The reaction between two 1,3-dialkylimidazolium-2-carboxylates 1a and 1b and two different dichlorophosphines (RPCl(2), with R = Ph and NEt(2)) led to new donor-stabilized phosphenium adducts. When the reaction was performed with the 1,3-dimethylimidazolium-2-carboxylate 1a and PhPCl(2) in a 2:1 ratio, the phosphine 4a, bearing two imidazolium moieties, was obtained and led to 5a, after an anion exchange reaction with KPF(6), the latter being fully characterized by an X-ray structure analysis. In similar conditions, the bis-imidazolium phosphine or phosphene-di-ium, 4b, which is analogous to 4a, has been obtained by the addition of PhPCl(2) to the 1-dodecyl-3-methylimidazolium-2-carboxylate…

Synthesis, reactivity and structures of ruthenium carbonyl clusters with telluride and hydride ligands

The reaction of [Cp* 2 Nb(Te 2 H)] ( 1 ) (Cp*=C 5 Me 5 ) with [Ru 3 (CO) 12 ] in boiling toluene gave [Ru 3 (μ 2 -H) 2 (CO) 9 (μ 3 -Te)] ( 2 ), [Ru 6 (μ 3 -H)(CO) 15 (μ 3 -Te) 3 ][Cp* 2 Nb(CO) 2 ] ( 3 ) and [Ru 5 (μ 2 -H)(CO) 14 (μ 4 -Te)][Cp* 2 Nb(CO) 2 ] ( 4 ) along with already known [Ru 4 (CO) 11 (μ 4 -Te) 2 ] ( 5 ). Complexes 2 – 4 were analytically and spectroscopically characterized and X-ray diffraction analyses of 3 and 4 were carried out. The anion of 3 is built up of a triangular hexametallic core of C 3 v symmetry, in which the central Ru 3 triangle, being bridged by a μ 3 -H ligand, is composed of three corner-linked Ru 3 Te tetrahedra. The main structural feature of the anion …

Aminomethyl-Substituted Ferrocenes and Derivatives: Straightforward Synthetic Routes, Structural Characterization, and Electrochemical Analysis

A variety of aminomethyl-substituted ferrocenes and the parent compounds (iminomethyl)ferrocenes, azaferrocenophanes, and diferrocenylamines can be selectively synthesized from reductive amination of 1,1′-diformylferrocene or formylferrocene. The optimized one- or two-step reactions have delivered 13 new compounds, isolated in 65–97% yields, which include tertiary (ferrocenylmethyl)amines and azaferrocenophanes by using NaBH(OAc)3 as a mild reducing agent and (iminomethyl)ferrocenes and secondary (ferrocenylmethyl)amines by using LiAlH4. X-ray structures of representative members of these ferrocene derivative families have evidenced the preferred conformation adopted by ferrocene backbones,…

Electrogeneration of Diiodoaurate in Dimethylsulfoxide on Gold Substrate and Localized Patterning

International audience; A localized etching of gold surface by scanning electrochemical microscope technique is presented where a dimethylsulfoxide-based electrolyte charged with iodine is used. The electrogenerated triiodide ion at the platinum ultramicroelectrode tip (feedback mode) acts as an oxidant for gold surface. The effects of electrode diameter and the bias time have been investigated. The approach curve method was used to hold the electrode tip close to the gold surface. A scanning electron microscope is used to observe the etched gold surfaces where disk-shaped dots are generated. The diameter of these holes depends directly on the Pt electrode diameter and the bias time.

Hexaphosphine: A Multifaceted Ligand for Transition Metal Coordination

We report the synthesis and characterization of the first ferrocenyl polyphosphane incorporating six phosphorus donor atoms. In this unique ligand, the cyclopentadienyl rings of the ferrocenyl backbone adopt a staggered position, which leads to a piano-stool arrangement for each of the two sets of three P atoms facing the same direction. As a consequence of its remarkable flexibility, this hexaphosphane displays versatile coordination behaviour towards metals, leading to unexpected structures of palladium and platinum bimetallic complexes. Analogous molybdenum and rhodium complexes are more classical.

Input of P, N-(phosphanyl, amino)-ferrocene hybrid derivatives in late transition metals catalysis

International audience; Unequally functionalized ferrocenes give access to valuable hemilabile reactivity in catalytic reaction. We address the synthesis of hybrid (P, N)-ferrocenyl compounds for which recent catalytic breakthrough applications have been reported, transversely in late transition metals chemistry. Palladium, nickel, rhodium, iridium, and emerging iron and gold catalysis are illustrated from selected examples, which include CC bond formation from cross-coupling and polymerization, allylic substitution, cyanation, hydroformylation, CH arylation and silylation and hydrogenation reactions.

Electron-Sponge Behavior and Electronic Structures in Cobalt-Centered Pentagonal Prismatic Co11Te7(CO)10 and Co11Te5(CO)15 Cluster Anions

The novel cluster anion [Co11Te5(CO)15]- ([3]-) has been isolated and structurally characterized as part of the salt [Cp*2Nb(CO)2][3] (Cp* = C5Me5). The cobalt-centered Co10 pentagonal prism is surrounded by a shell of two μ5-Te, three μ4-Te ligands, and 15 CO groups in terminal, symmetrical, and σ-semibridging bonding modes. The hybrid carbonyl-telluride character of the ligand shell is reflected in the solid state by a one-dimensional assembly of polyhedral prisms along a backbone of [Cp*2Nb(CO)2]+ cations. Electrochemical studies reveal the presence of four redox couples of [3]n (n = −1 to −5). The electronic structures of various metal-centered and empty pentagonal-prismatic (PP) M10 cl…

First donor stabilized-phosphenium copper(I) complexes

Abstract The preliminary studies of coordination properties of one donor stabilized-phosphenium adduct have been explored in copper chemistry. The preparation as well as the characterization of first examples of donor stabilized-phosphenium copper(I) complexes is reported in the paper. Thus, the direct addition of CuBr.SMe2 to an equivalent amount of cationic P‐ligands (L1+ or L2+)(PF6), with and , following by a crystallization in acetonitrile/Et2O led to first copper complexes [(L1,2+)CuBr2−] 1 and 3 and [(L1,2+)Cu+(NCMe)3+](PF6−)2 2 and 4 in a 1:1 ratio. However, when DMF/Et2O mixture was used as crystallization solvent, a stable bromo-bridged copper(I) dimer 5 [(L2+)CuBr(DMF)]2 was obta…

Triorganotin( iv ) cation-promoted dimethyl carbonate synthesis from CO 2 and methanol: solution and solid-state characterization of an unexpected diorganotin( iv )-oxo cluster

Two novel C,N-chelated organotin(IV) complexes bearing weakly coordinating carborane moieties were prepared by the reaction of the corresponding C,N-chelated organotin(IV) chloride (i.e. LCNR2SnCl, R = n-Bu (1) and Ph (2); LCN = 2-(N,N-dimethylaminomethyl)phenyl)) with monocarba-closo-dodecaborate silver salt (AgCB11H12; Ag·3). Both products of the metathesis, [LCN(n-Bu)2Sn]+[CB11H12]− (4) and [LCNPh2Sn]+ [CB11H12]− (5), respectively, were characterized by both multinuclear NMR spectroscopy and elemental analysis. The instability of 4 and 5 towards water is discussed. The solid-state structure of LCN(n-Bu)2SnOH·B(C6F5)3 (4a) as a model compound with a Sn–O(H)⋯B linkage is also reported. The…

Preparative and Electrochemical Investigations on the Electron Sponge Behavior of Cobalt Telluride Clusters: CO Substitution in[Co11Te7(CO)10]n− Ions (n=1, 2) by PMe2Ph and Crystal Structure of[Co11Te7(CO)5(PMe2Ph)5]

The reaction of the cluster salts [Cp* 2 Nb(CO) 2 ] n [Co 1 1 Te 7 (CO) 1 0 ] (Cp* = C 5 Me 5 ; n = 1, 2) with excess PMe 2 Ph gave the neutral, dark brown clusters [Co 1 1 Te 7 (CO) 6 (PMe 2 Ph) 4 ] (5) and [Co 1 1 Te 7 (CO) 5 (PMe 2 Ph) 5 ] (6) with 147 metal valence electrons. The new compounds were characterized by IR spectroscopy, elemental analyses, and mass spectrometry. The molecular structure of 6 was determined by X+ray crystallography. Like its precursor anion, it consists of a pentagonal-prismatic [Co 1 1 Te 7 ] core, but with a ligand sphere composed of five CO and five PMe 2 Ph ligands. Detailed electrochemical studies of both reactions reveal that a stepwise substitution of C…

A general diastereoselective synthesis of highly functionalized ferrocenyl ambiphiles enabled on a large scale by electrochemical purification

International audience; A general synthesis of highly functionalized ferrocenes, which include (P,B)- and (N,B)-ambiphiles, has been developed at a multigram scale. Diastereoselective stepwise modification of di-tert-butylated ferrocenes included the unprecedented separation of electroactive species. Bulky alkyl groups on ferrocenes ensure planar chirality of ambiphiles and enforce closer proximity of antagonist Lewis functions.

Di-n-butyltin oxide as a chemical carbon dioxide capturer

Abstract Several synthetic routes to the decakis(di-n-butyltin(IV)) oxocluster, (n-Bu2SnO)6[(n-Bu2SnOCH3)2(CO3)]2 (1), a diorganotin compound previously shown to belong to the class of organotins able to store carbon dioxide, as well as its reactivity toward dimethyl carbonate (DMC), are described. The synthetic route from n-Bu2SnO and DMC was applied for the preparation of the ethoxy analogue of 1, oxocluster 2, using diethyl carbonate. The structural relationship connecting cluster 1, with its precursor PRE-1 isolated from recycling experiments and n-Bu2SnO is discussed. For this purpose, the reactivity of PRE-1 with trifluoromethanesulfonic acid was investigated in order to trace structu…

Crystallographic and (spectro)electrochemical characterizations of cobalt(II) 10-phenyl-5,15-di-p-tolylporphyrin

International audience; The synthesis, cyclic and rotating disk electrode voltammograms, UV-visible absorption and Xray diffraction analyses of cobalt(II) 10-phenyl-5,15-dip -tolylporphyrin (1-Co) are described. 1-Co was crystallized by slow diffusion of n-hexane into a concentrated CH2Cl2 solution. X-ray diffraction analyses reveals porphyrin aromatic cycle stacking in the crystal, C-H•••π interactions of the CH2Cl2 solvent with the π-system of one tolyl group and Co(II)•••π (porphyrin ring) interactions. The abstraction of 1.0 F/mol during the electrolysis at the first oxidation potential was followed by spectroelectrochemistry. It leads to the Co(II) → Co(III) transformation rather than …

Bis(η-tert-butylcyclopentadienyl)hydridoniobium Ditelluride, a Convenient Reagent for the Synthesis of Polynuclear Metal Telluride Complexes

Conformational Control of Metallocene Backbone by Cyclopentadienyl Ring Substitution: a New Concept in Polyphosphane Ligands Evidenced by “Through-Space” Nuclear Spin-Spin Coupling. Application in heteroaromatics arylation by direct C–H activation

The present study deals with the conformational control of the metallocene backbone within ferrocenyl polyphosphane ligands and their performance in the highly topical palladium-catalyzed heteroaromatics arylation by direct C−H activation. New substituted cyclopentadienyl rings were synthesized, which allowed the assembling of original tri- and diphosphanes. The bulky cyclopentadienyl lithium salts diphenylphosphino-3-(triphenyl)methylcyclopentadienyllithium (4) and 1,2-bis(diphenylphosphino)-4-(triphenyl)methylcyclopentadienyllithium (5) were prepared in excellent yield. The assembling of these new hindered cyclopentadienyl salts (Cp) with other Cp fragments was performed in order to prepa…

Synthesis and structural characterisation of bulky heptaaromatic (hetero)aryl o-substituted s-aryltetrazines

An expedient two-step synthesis produces in good yield polyaromatic heptacyclic (hetero)arylated o-substituted s-aryltetrazines (s-Tz) directly from diphenyl s-tetrazine. This methodology overcomes the steric limitations of classical Pinner-like syntheses encountered for o-functionalized s-Tz. A single step palladium-catalyzed N-directed C–H bond tetrahalogenation is followed by a Pd-catalyzed Suzuki (hetero)arylation that is achieved simultaneously on four sites. The single crystal X-ray diffraction structure of the resulting typical polyaromatic heptacyclic aromatic compound 3,6-bis(2,6-diphenyl)-1,2,4,5-tetrazine (3) is analyzed, together with R-functionalized peripheral phenyl derivativ…

Oxidative C-N fusion of pyridinyl-substituted porphyrins.

International audience; The mild (electro) chemical oxidation of pyridin-2-ylthio-meso substituted Ni(II) porphyrins affords C-N fused cationic and dicationic pyridinium-based derivatives. These porphyrins are fully characterized and the molecular structure of one of them was confirmed by X-ray crystallography. A mechanism for the intramolecular oxidative C-N coupling is proposed based on theoretical calculations and cyclic voltammetry analyses.

A sterically congested 1,2-diphosphino-1'-boryl-ferrocene: synthesis, characterization and coordination to platinum.

International audience; A new class of tritopic ferrocene-based ambiphilic compound has been prepared by assembling diphosphino- and boryl-substituted cyclopentadienides at iron. The presence of five sterically demanding substituents on the ferrocene platform induces conformation constraints, as apparent from XRD and NMR data, but does not prevent chelating coordination to platinum. The Lewis acid moiety is pendant in both the free ligand and the platinum complex.

Congested ferrocenyl polyphosphanes bearing electron-donating or electron-withdrawing phosphanyl groups: assessment of metallocene conformation from NMR spin couplings and use in palladium-catalyzed chloroarenes activation.

International audience; The synthesis of novel substituted cyclopentadienyl salts that incorporate both a congested branched alkyl group (tert-butyl, (triphenyl)methyl, or tri(4-tert-butyl)phenylmethyl) and a phosphanyl group is reported. The introduction of either electron-withdrawing or electron-donating substituents (furyl, i-propyl, cyclohexyl, tert-butyl) on P atoms was generally achieved in high yield. The modular synthesis of ferrocenyl polyphosphanes from an assembly of these cyclopentadienyl salts was investigated, leading to the formation of new triphosphanes (denoted as 9-12) and diphosphanes (denoted as 14-16). The resulting phosphanes are not sensitive to air or moisture, even …

Catena-poly[[di-n-butyltin(IV)]-mu-trifluoromethanesulfonato-[[di-n-butyl(trifluoromethanesulfonato)tin(IV)]-di-mu-hydroxo]]

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Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols

Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were o…

Regioselective C–H amination of free base porphyrins via electrogenerated pyridinium-porphyrins and stabilization of easily oxidized amino-porphyrins by protonation

Four free base aminoporphyrins were synthesized in two steps via regioselective anodic nucleophilic substitution with pyridine followed by ring opening of the electrogenerated pyridinium with piperidine. The X-ray crystallographic structure of the unstable 2-aminotetraphenylporphyrin was solved. Protonation of this latter compound leads to the stable diiminium porphyrin salt.

A novel two-dimensional organostannoxane coordination network promoted by phenazine: Synthesis, characterization and X-ray structure of

Abstract Reaction of the dimeric hydroxo di-n-butylstannane trifluoromethanesulfonato complex [n-Bu2Sn(μ-OH)(H2O)0.5(η1-O3SCF3)]2 (1) with phenazine (C12H8N2, Phz) (2) in dichloromethane at room temperature in a 1:3 molar ratio yielded the novel two-dimensional organometallic coordination polymer 2 ∞ { [ n - Bu 2 ( μ -OH ) SnOSn ( μ - η 2 - O 3 SCF 3 ) n - Bu 2 ] 2 [ n - Bu 2 ( μ -OH ) SnOSn ( η 1 - O 3 SCF 3 ) n - Bu 2 ] 2 } (3), together with the phenazinium trifluoromethanesulfonate salt [C12H9N2]+ [CF3SO3]−, crystallographically isolated in two different structural arrangements, free 4 and in π–π aromatic stacking interaction with independent intercalated non-protonated phenazine molecu…

Ethylammonium hydrogen oxalate–oxalic acid (2/1)

The reaction between ethylamine and oxalic acid in water in a 1:1 molar ratio afforded the title salt, C2H8N+·C2HO4 −·0.5C2H2O4. The hydrogen oxalate anions interact through hydrogen bonding and are organized into a chains propagating along the c-axis direction. The chains are connected to the neighbouring cations and oxalic acid molecules by N—H...O and O—H...O hydrogen bonds and N...O dipole–dipole contacts, leading to a supramolecular three-dimensional network.

Unsymmetrically Substituted Bis(phosphino)Ferrocenes Triggering Through-Space 31(P, P′)-Nuclear Spin Couplings and Encapsulating Coinage Metal Cations

International audience; We describe unsymmetrically substituted di-tert-butylated 1,1'-bis(phosphino)ferrocenes, with phosphino substituents R = [5-methyl]-2-furyl = Fu, and R' = phenyl (4a), i-propyl (4b). A modular synthetic approach was applied from the di-tert-butylated ferrocene platform (1), which lead to the formation of new diphosphines by using 1,1'bis(diiodo)-3,3'-bis(tert-butyl)ferrocene (2) as synthetic precursor. In contrast to the cousin non-alkylated unsymmetrically substituted diphosphino-ferrocenes which were reported up to now, these diphosphines showed strong (31 P, P')nonbonded (" ug-p e") nuclear spin-spin coupling. The strength of such internuclear spin-spin coupling c…

Crystal structure of dimethylammonium hydrogen oxalate hemi(oxalic acid)

The title salt consists of a di­methyl­ammonium cation (Me2NH2 +), an hydrogenoxalate anion (HC2O4 −), and half a mol­ecule of oxalic acid (H2C2O4) situated about an inversion center. They are linked together through inter­molecular hydrogen bonds, forming a two-dimensional bilayer-like self-assembly.

Coordination Chemistry of a Bis(Tetrazine) Tweezer: A Case of Host-Guest Behavior with Silver Salts

The carbon-carbon cross-coupling of phenyl s-tetrazine (Tz) units at their ortho-phenyl positions allows the formation of constrained bis(tetrazines) with original tweezer structures. In these compounds, the face-to-face positioning of the central tetrazine cores is reinforced by π-stacking of the electron-poor nitrogen-containing heteroaromatic moieties. The resulting tetra-aromatic structure can be used as a weak coordinating ligand with cationic silver. This coordination generates a set of bis(tetrazine)-silver(I) coordination complexes tolerating a large variety of counter anions of various geometries, namely, PF6−, BF4−, SbF6−, ClO4−, NTf2−, and OTf−. These compounds were characterized…

Modular functionalized polyphosphines for supported materials: previously unobserved (31)P-NMR «through-space» ABCD spin systems and heterogeneous palladium-catalysed C-C and C-H arylation.

The modular design of polyphosphines, diversely functionalized for facile immobilization on virtually any kind of support, is reported. Previously unobserved ABCD (31)P NMR spin-spin systems evidence the control exercised on the polyphosphines conformation. We illustrate the catalytic performance at low Pd loading of the recyclable immobilized polyphosphines in C-C bond formation reactions.

Bio-based 1,3-diisobutyl imidazolium hydrogen oxalate [iBu 2 IM](HC 2 O 4 ) as CO 2 shuttle

International audience; This manuscript describes the using of biosourced L-valine, oxalic acid and glyoxal to produce a biobased imidazolium hydrogen oxalate [iBu(2)IM](HC2O4) which is converted to its related hydrogen carbonate salt by a simple electrolysis without using strong base. The addition of weak protic acids to the latter compound leads to a rapid and quantitative CO2 release with formation of the starting hydrogen oxalate salt or a new halide free bio-based ionic liquid [iBu(2)IM](AcO) which is able to adsorb reversibly the CO2 at room temperature. The protonation reactions, combined with electrolysis, could then be a promising alternative solution for storage and transport of C…

Selective formation of a unique diphosphonium-diphosphine from a tetraphosphine double protonation induced by zirconium salts

A mixed ferrocenyl diphosphonium-diphosphine cation, associated with two [ZrCl(5).thf](-) anions, is obtained from a ferrocenyl tetraphosphine, as a unique didentate ionic metalloligand in a perfectly selective reaction induced by ZrCl(4) in THF.

Electrosynthesis as a powerful method for the generation of catalytic intermediates: efficient isolation of a palladium aryl halide oxidative addition product.

International audience; Polyphosphane ligands of controlled conformation promote highly efficient palladium-catalyzed cross-coupling reactions. Electrosynthesis has been used as a new straightforward method to obtain important intermediates in the search for a better mechanistic understanding. As a proof of concept, the facile synthesis of a phenyl iodopalladium(II) complex (2) was conducted at the electrolysis scale from a readily electrogenerated unstable Pd0 precursor.

Structural characterization of 2,2-di-n-butyl-4-methyl-1,3,2-dioxastannolane isolated from supercritical CO2 conditions

The title compound has been isolated as single crystals from the synthesis of propylene carbonate from racemic 1,2-propanediol and carbon dioxide using n-Bu2SnO as a catalyst precursor. The X-ray crystallographic structure analysis revealed the self-assembly of di-n-butyltin(IV) 1,2-propanediolate units, linked together through long-distance Sn-O interactions leading to a one-dimensional polymeric architecture organized in a syndiotactic arrangement. The coordination geometry around the tin atoms can be described as an unusual faced-capped trigonal bipyramidal environment.

Crystal structure of the diglycidyl ether of eugenol

The diep­oxy monomer (DGE-Eu) was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-tris­ubstituted benzene ring substituted by diglycidyl ether, a meth­oxy group and a methyl­oxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ab plane.

Ferrocenyl (P,N)-diphosphines incorporating pyrrolyl, imidazolyl or benzazaphospholyl moieties: Synthesis, coordination to group 10 metals and performances in palladium-catalyzed arylation reactions

Abstract Three novel symmetrical ferrocenyl diphosphines with tertiary phosphorus atoms holding respectively nitrogen-containing heterocyclic derivatives of pyrrole, imidazole and benzazaphosphole were synthesized and characterized. Up to now, integration of heteroaromatic fragments, or more generally hetero-cycles, as substituents on the tertiary phosphines of symmetrical ferrocenyl diphosphines has been limited to the furyl motif. Their coordination to palladium and platinum group 10 transition metals was exemplified, and analyzed using single crystal X-ray diffraction. The performances obtained in palladium-catalyzed copper-free Sonogashira and Suzuki cross-coupling reactions using bromo…

Organotin(IV) selenate derivatives – Crystal structure of [{(Ph 3 Sn) 2 SeO 4 } ⋅ CH 3 OH] n

Abstract Crystallization of [(Ph3Sn)2SeO4] ⋅ 1.5H2O in methanol leads to the formation of [{(Ph3Sn)2SeO4} ⋅ CH3OH] n (1) which constitutes a new specimen of organotin(IV) selenate derivatives. In the solid state, complex 1 is arranged in polymeric zig-zag chains, composed of alternating Ph3Sn and SeO4 groups. In addition, pendant Ph3Sn ⋅ CH3OH moieties are branched along chains according to a syndiotactic organization and via Sn-O-Se connections. From a supramolecular point of view, intermolecular hydrogen bonds established between the selenate groups (uncoordinated oxygen) and the hydroxyl functions (CH3OH) of the pendant groups link the chains together.

Phosphorus‐Directed Rhodium‐Catalyzed C−H Arylation of 1‐Pyrenylphosphines Selective at the K ‐Region

Converging and Diverging Synthetic Strategies to Tetradentate (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation

Hexasubstituted hybrid tetradentate (N,N′,P,P′)-ferrocenes bearing phosphino and aminomethyl groups, plus hindering tert-butyl moieties, were synthesized by using two different strategies: a “diverging” synthesis involving successive functionalization of preformed di-tert-butylated ferrocene and a “converging” assembly of the species from appropriately substituted cyclopentadienyl rings. While the new cyclopentadienyl salts formed are of interest, their assembly with iron dichloride used as a “converging” way to produce tetradentate ferrocene ligands presented several drawbacks. Conversely, the synthesis of new tert-butylated (aminomethyl)ferrocene derivatives was found convenient to furthe…

Two new organic-selenate salts: syntheses and crystal structures of bis(di-iso-propylammonium) selenate and di-n-butylammonium hydrogenoselenate

Abstract Two new dialkyammonium selenate salts [i-Pr2NH2]2[SeO4] (1) and [n-Bu2NH2][HSeO4] (2) have been isolated and characterized by single-crystal X-ray diffraction. Salt 1 crystallizes in the monoclinic system, space group P21/n with a=8.7190(5), b=8.8500(4), c=22.5953(9) Å, β=94.6290(17)°, V=1737.84(14) Å3 and Z=4. Salt 2 crystallizes in the monoclinic system space group P21/n with a=10.9328(9), b=8.1700(6), c=13.8095(11) Å, β=97.130(3)°, V=1223.94(17) Å3 and Z=4. In both salts, dialkylammonium cations and selenate anions are connected through NH···O and OH···O hydrogen bonds. In the crystal structure, 1 and 2 are organized in layer-like arrangements. Structural characterizations were …

Bridge-Clamp Bis(tetrazine)s with [N] 8 π-Stacking Interactions and Azido- s -Aryl Tetrazines: Two Classes of Doubly Clickable Tetrazines

Click chemistry at a tetrazine core is useful for bioorthogonal labeling and crosslinking. Introduced here are two new classes of doubly clickable s-aryl tetrazines synthesized by Cu-catalyzed cross-coupling. Homocoupling of o-brominated s-aryl tetrazines leads to bis(tetrazine)s structurally characterized by tetrazine cores arranged face-to-face. [N]8 π-stacking interactions are essential to the conformation. Upon inverse electron demand Diels-Alder (iEDDA) cycloaddition, the bis(tetrazine)s produce a unique staple structure. The o-azidation of s-aryl tetrazines introduces a second proximal intermolecular clickable function that leads to double click chemistry opportunities. The stepwise i…

Electrochemical meso-functionalization of magnesium(II) porphine

International audience; Regioselective meso-functionalization of the totally unsubstituted magnesium(II) porphine was performed by controlled potential electrolysis with pyridine and triphenylphosphine as nucleophiles leading to the original pyridinium and phosphonium substituted derivatives, respectively. The crystallographic structure of the latter is described as the only meso-phosphonium porphyrin reported to date.

First copper(I) ferrocenyltetraphosphine complexes: possible involvement in Sonogashira cross-coupling reaction ?

Preparation and characterization of the first examples of copper(I) ferrocenylpolyphosphine complexes are reported. The molecular structure of complex {P,P′,P′′-[1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene]iodocopper(I)} (1) was solved by X-ray diffraction studies, and its fluxional behavior in solution was investigated by VT-31P NMR; both revealed a net triligated coordination preference of the ferrocenyl tetraphosphine Fc(P)4tBu with copper. The tetradentate ligand is an active auxiliary in Sonogashira alkynylation; therefore the general question of copper as a competitive coordination partner in the Pd/Cu-catalyzed Sonogashira reaction was raised and discussed. Elec…

Highly Functionalized Brønsted Acidic/Lewis Basic Hybrid Ferrocene Ligands: Synthesis and Coordination Chemistry

International audience; A general challenging issue in the synthesis of hemilabile ferrocene ligands is the access to highly functionalized ferrocene starting materials. These can bear donor/acceptor atoms, additional functional and structuring spectator substituents, but the preparation of such species poses general synthetic difficulties. We report herein alternative synthetic routes to hybrid ferrocene donors such as tert-butylated phosphanylcarboxylic acids and their corresponding aldehydes. These hybrid ambiphilic species that combine Brønsted-acidic and Lewis-basic functional moieties in their structure were characterized by multinuclear NMR and single-crystal X-ray diffraction analys…

Electron-Sponge Behavior, Reactivity and Electronic Structures of Cobalt-Centered Cubic Co9Te6(CO)8 Clusters

Extended investigations of the reaction sequence [Cp′2Nb(Te2)H]/CH3Li/[Co2(CO)8] (Cp′ = tBuC5H4) led to the identification of Lin[3] {3 = [Co9Te6(CO)8]; n = 1, 2} salts through their transformation with [PPN]Cl into [PPN]n[3] (PPN = Ph3PNPPh3). These compounds form in the solid state columnar ([PPN][3]) or undulated 2D ([PPN]2[3]) supramolecular networks. Electrochemical studies of [Cp*2Nb(CO)2][3] (Cp* = C5Me5) or [Na(THF)6][3] revealed the presence of the redox couples [3]–/[3]2–/[3]3–/[3]4–/[3]5– regardless of the nature of the cation, whereas in the anodic part oxidative degradation of the cluster takes place. This behavior is in agreement with the observation that [3]– containing salts…

Reappraising Schmidpeter's bis(iminophosphoranyl)phosphides: coordination to transition metals and bonding analysis

The synthesis and characterization of a range of bis(iminophosphoranyl)phosphide (BIPP) group 4 and coinage metals complexes is reported. BIPP ligands bind group 4 metals in a pseudo fac-fashion, and the central phosphorus atom enables the formation of d0–d10 heterobimetallic complexes. Various DFT computational tools (including AIM, ELF and NCI) show that the phosphorus–metal interaction is either electrostatic (Ti) or dative (Au, Cu). A bridged homobimetallic Cu–Cu complex was also prepared and its spectroscopic properties were investigated. The theoretical analysis of the P–P bond in BIPP complexes reveals that (i) BIPP are closely related to ambiphilic triphosphenium (TP) cations; (ii) …

CCDC 1054568: Experimental Crystal Structure Determination

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CCDC 1868748: Experimental Crystal Structure Determination

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CCDC 1433505: Experimental Crystal Structure Determination

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CCDC 1983790: Experimental Crystal Structure Determination

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CCDC 922383: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nikolay V. Vologdin, Hélène Cattey, Nadine Pirio, Daoud Naoufal, Ali Kanj, Radomyr V. Smaliy, Aleksandr Savateev, Anatoly Marchenko, Anastasia Hurieva, Heorgii Koidan, Aleksandr N. Kostyuk, Jean-Cyrille Hierso|2013|J.Organomet.Chem.|735|38|doi:10.1016/j.jorganchem.2013.03.025

CCDC 1532854: Experimental Crystal Structure Determination

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CCDC 1828692: Experimental Crystal Structure Determination

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CCDC 2109022: Experimental Crystal Structure Determination

Related Article: Charline Sire, Hélène Cattey, Anthonia Tsivery, Jean‐Cyrille Hierso, Julien Roger|2022|Adv.Synth.Catal.|364|440|doi:10.1002/adsc.202101211

CCDC 1978292: Experimental Crystal Structure Determination

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CCDC 1590298: Experimental Crystal Structure Determination

Related Article: Petr Švec, Hélène Cattey, Zdeňka Růžičková, Josef Holub, Aleš Růžička, Laurent Plasseraud|2018|New J.Chem.|42|8253|doi:10.1039/C7NJ05058E

CCDC 1433497: Experimental Crystal Structure Determination

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CCDC 1978293: Experimental Crystal Structure Determination

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CCDC 1908608: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1908609: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 952665: Experimental Crystal Structure Determination

Related Article: Naima Khiri-Meribout, Etienne Bertrand, Jérôme Bayardon, Marie-Joëlle Eymin, Yoann Rousselin, Hélène Cattey, Daniel Fortin, Pierre D. Harvey, and Sylvain Jugé|2013|Organometallics|32|2827|doi:10.1021/om400229p

CCDC 1433499: Experimental Crystal Structure Determination

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CCDC 988195: Experimental Crystal Structure Determination

Related Article: Matthieu Beaupérin, Radomyr Smaliy, Hélène Cattey, Philippe Meunier, Jun Ou, Patrick H. Toy, Jean-Cyrille Hierso|2014|Chem.Commun.|50|9505|doi:10.1039/C4CC04307C

CCDC 939068: Experimental Crystal Structure Determination

Related Article: Guillaume de Robillard, Charles H. Devillers, Doris Kunz, Hélène Cattey, Eric Digard, and Jacques Andrieu|2013|Org.Lett.|15|4410|doi:10.1021/ol401949f

CCDC 1919134: Experimental Crystal Structure Determination

Related Article: Julie Echaubard, Asmae Bousfiha, Mathieu Berthelot, Julien Roger, Paul Fleurat-Lessard, Hélène Cattey, Sophie Fournier, Charles H. Devillers, Dominique Lucas|2020|Eur.J.Inorg.Chem.|2020|551 |doi:10.1002/ejic.201900849

CCDC 2006293: Experimental Crystal Structure Determination

Related Article: Abdou K.D. Dimé, Hélène Cattey, Dominique Lucas, Charles H. Devillers|2020|J.Mol.Struct.|1226|129321|doi:10.1016/j.molstruc.2020.129321

CCDC 1877098: Experimental Crystal Structure Determination

Related Article: Léa Radal, Petr Vosáhlo, Julien Roger, Hélène Cattey, Régine Amardeil, Ivana Císařová, Petr Štěpnička, Nadine Pirio, Jean‐Cyrille Hierso|2019|Eur.J.Inorg.Chem.||865|doi:10.1002/ejic.201801378

CCDC 1485963: Experimental Crystal Structure Determination

Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583

CCDC 1919135: Experimental Crystal Structure Determination

Related Article: Julie Echaubard, Asmae Bousfiha, Mathieu Berthelot, Julien Roger, Paul Fleurat-Lessard, Hélène Cattey, Sophie Fournier, Charles H. Devillers, Dominique Lucas|2020|Eur.J.Inorg.Chem.|2020|551 |doi:10.1002/ejic.201900849

CCDC 1532860: Experimental Crystal Structure Determination

Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Charles H. Devillers, Dominique Lucas, Jean-Cyrille Hierso|2017|Chem.Commun.|53|6017|doi:10.1039/C7CC02469J

CCDC 980179: Experimental Crystal Structure Determination

Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s

CCDC 980175: Experimental Crystal Structure Determination

Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s

CCDC 1828690: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1868745: Experimental Crystal Structure Determination

Related Article: Florian Chotard, Rosita Lapenta, Anaëlle Bolley, Audrey Trommenschlager, Cédric Balan, Jérôme Bayardon, Raluca Malacea-Kabbara, Quentin Bonnin, Ewen Bodio, Hélène Cattey, Philippe Richard, Stefano Milione, Alfonso Grassi, Samuel Dagorne, Pierre Le Gendre|2019|Organometallics|38|4147|doi:10.1021/acs.organomet.9b00501

CCDC 1978288: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Raluca Malacea-Kabbara, Rosita Lapenta, Aymeric Dajnak, Philippe Richard, Hélène Cattey, Anaëlle Bolley, Alfonso Grassi, Stefano Milione, Audrey Auffrant, Samuel Dagorne, Pierre Le Gendre|2020|Dalton Trans.|49|6989|doi:10.1039/D0DT00972E

CCDC 1978291: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Raluca Malacea-Kabbara, Rosita Lapenta, Aymeric Dajnak, Philippe Richard, Hélène Cattey, Anaëlle Bolley, Alfonso Grassi, Stefano Milione, Audrey Auffrant, Samuel Dagorne, Pierre Le Gendre|2020|Dalton Trans.|49|6989|doi:10.1039/D0DT00972E

CCDC 1978295: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Raluca Malacea-Kabbara, Rosita Lapenta, Aymeric Dajnak, Philippe Richard, Hélène Cattey, Anaëlle Bolley, Alfonso Grassi, Stefano Milione, Audrey Auffrant, Samuel Dagorne, Pierre Le Gendre|2020|Dalton Trans.|49|6989|doi:10.1039/D0DT00972E

CCDC 1557313: Experimental Crystal Structure Determination

Related Article: Mathieu Berthelot, Guillaume Hoffmann, Asmae Bousfiha, Julie Echaubard, Julien Roger, Hélène Cattey, Anthony Romieu, Dominique Lucas, Paul Fleurat-Lessard, Charles H. Devillers|2018|Chem.Commun.|54|5414|doi:10.1039/C8CC01375F

CCDC 1433506: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601

CCDC 1848218: Experimental Crystal Structure Determination

Related Article: Abdou K. D. Dimé, Hélène Cattey, Dominique Lucas, Charles H. Devillers|2018|Eur.J.Org.Chem.|2018|4834|doi:10.1002/ejic.201801142

CCDC 1433503: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601

CCDC 1433501: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601

CCDC 1985146: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H

CCDC 1433498: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601

CCDC 1985142: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H

CCDC 1983787: Experimental Crystal Structure Determination

Related Article: Tuan‐Anh Nguyen, Julien Roger, Houssein Nasrallah, Vincent Rampazzi, Sophie Fournier, Hélène Cattey, E. Daiann Sosa Carrizo, Paul Fleurat‐Lessard, Charles H. Devillers, Nadine Pirio, Dominique Lucas, Jean‐Cyrille Hierso|2020|Chem.Asian J.|15|2879|doi:10.1002/asia.202000579

CCDC 1433504: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601

CCDC 981913: Experimental Crystal Structure Determination

Related Article: Abdou K. D. Dimé, Charles H. Devillers, Hélène Cattey, Dominique Lucas|2014|Dalton Trans.|43|14554|doi:10.1039/C4DT00221K

CCDC 1868749: Experimental Crystal Structure Determination

Related Article: Florian Chotard, Rosita Lapenta, Anaëlle Bolley, Audrey Trommenschlager, Cédric Balan, Jérôme Bayardon, Raluca Malacea-Kabbara, Quentin Bonnin, Ewen Bodio, Hélène Cattey, Philippe Richard, Stefano Milione, Alfonso Grassi, Samuel Dagorne, Pierre Le Gendre|2019|Organometallics|38|4147|doi:10.1021/acs.organomet.9b00501

CCDC 1985138: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H

CCDC 1877102: Experimental Crystal Structure Determination

Related Article: Léa Radal, Petr Vosáhlo, Julien Roger, Hélène Cattey, Régine Amardeil, Ivana Císařová, Petr Štěpnička, Nadine Pirio, Jean‐Cyrille Hierso|2019|Eur.J.Inorg.Chem.||865|doi:10.1002/ejic.201801378

CCDC 1978290: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Raluca Malacea-Kabbara, Rosita Lapenta, Aymeric Dajnak, Philippe Richard, Hélène Cattey, Anaëlle Bolley, Alfonso Grassi, Stefano Milione, Audrey Auffrant, Samuel Dagorne, Pierre Le Gendre|2020|Dalton Trans.|49|6989|doi:10.1039/D0DT00972E

CCDC 1978289: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, Raluca Malacea-Kabbara, Rosita Lapenta, Aymeric Dajnak, Philippe Richard, Hélène Cattey, Anaëlle Bolley, Alfonso Grassi, Stefano Milione, Audrey Auffrant, Samuel Dagorne, Pierre Le Gendre|2020|Dalton Trans.|49|6989|doi:10.1039/D0DT00972E

CCDC 1532862: Experimental Crystal Structure Determination

Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Charles H. Devillers, Dominique Lucas, Jean-Cyrille Hierso|2017|Chem.Commun.|53|6017|doi:10.1039/C7CC02469J

CCDC 1590299: Experimental Crystal Structure Determination

Related Article: Petr Švec, Hélène Cattey, Zdeňka Růžičková, Josef Holub, Aleš Růžička, Laurent Plasseraud|2018|New J.Chem.|42|8253|doi:10.1039/C7NJ05058E

CCDC 1985584: Experimental Crystal Structure Determination

Related Article: Laurent Plasseraud, Hélène Cattey|2020|Main Group Met.Chem.|43|102|doi:10.1515/mgmc-2020-0012

CCDC 1474154: Experimental Crystal Structure Determination

Related Article: Emmanuel Lerayer, Patrice Renaut, Stéphane Brandès, Hélène Cattey, Paul Fleurat-Lessard, Ghenwa Bouhadir, Didier Bourissou, and Jean-Cyrille Hierso|2017|Inorg.Chem.|56|1966|doi:10.1021/acs.inorgchem.6b02510

CCDC 1985136: Experimental Crystal Structure Determination

Related Article: Adrien T. Normand, E. Daiann Sosa Carrizo, Corentin Magnoux, Esteban Lobato, Hélène Cattey, Philippe Richard, Stéphane Brandès, Charles H. Devillers, Anthony Romieu, Pierre Le Gendre, Paul Fleurat-Lessard|2021|Chemical Science|12|253|doi:10.1039/D0SC04736H

CCDC 1993888: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Ahmad Daher, Neelab Khirzada, Charles H. Devillers, Hélène Cattey, Paul Fleurat-Lessard, Julien Roger, Jean-Cyrille Hierso|2020|New J.Chem.|44|15235|doi:10.1039/D0NJ02338H

CCDC 1009244: Experimental Crystal Structure Determination

Related Article: Andrey A. Fokin, Raisa I. Yurchenko, Boryslav A. Tkachenko, Natalie A. Fokina, Maria A. Gunawan, Didier Poinsot, Jeremy E. P. Dahl , Robert M. K. Carlson , Michael Serafin , Hélène Cattey, Jean-Cyrille Hierso , and Peter R. Schreiner|2014|J.Org.Chem.|79|5369|doi:10.1021/jo500793m

CCDC 1908612: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 943311: Experimental Crystal Structure Determination

Related Article: Anatolyi Marchenko, Anastasiya Hurieva, Heorgii Koidan, Vincent Rampazzi, Hélène Cattey, Nadine Pirio, Aleksandr N. Kostyuk, and Jean-Cyrille Hierso|2012|Organometallics|31|5986|doi:10.1021/om300563n

CCDC 2109009: Experimental Crystal Structure Determination

Related Article: Charline Sire, Hélène Cattey, Anthonia Tsivery, Jean‐Cyrille Hierso, Julien Roger|2022|Adv.Synth.Catal.|364|440|doi:10.1002/adsc.202101211

CCDC 1485958: Experimental Crystal Structure Determination

Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583

CCDC 1991440: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Ahmad Daher, Neelab Khirzada, Charles H. Devillers, Hélène Cattey, Paul Fleurat-Lessard, Julien Roger, Jean-Cyrille Hierso|2020|New J.Chem.|44|15235|doi:10.1039/D0NJ02338H

CCDC 1877097: Experimental Crystal Structure Determination

Related Article: Léa Radal, Petr Vosáhlo, Julien Roger, Hélène Cattey, Régine Amardeil, Ivana Císařová, Petr Štěpnička, Nadine Pirio, Jean‐Cyrille Hierso|2019|Eur.J.Inorg.Chem.||865|doi:10.1002/ejic.201801378

CCDC 980177: Experimental Crystal Structure Determination

Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s

CCDC 922384: Experimental Crystal Structure Determination

Related Article: Fatima Allouch, Nikolay V. Vologdin, Hélène Cattey, Nadine Pirio, Daoud Naoufal, Ali Kanj, Radomyr V. Smaliy, Aleksandr Savateev, Anatoly Marchenko, Anastasia Hurieva, Heorgii Koidan, Aleksandr N. Kostyuk, Jean-Cyrille Hierso|2013|J.Organomet.Chem.|735|38|doi:10.1016/j.jorganchem.2013.03.025

CCDC 1983797: Experimental Crystal Structure Determination

Related Article: Tuan‐Anh Nguyen, Julien Roger, Houssein Nasrallah, Vincent Rampazzi, Sophie Fournier, Hélène Cattey, E. Daiann Sosa Carrizo, Paul Fleurat‐Lessard, Charles H. Devillers, Nadine Pirio, Dominique Lucas, Jean‐Cyrille Hierso|2020|Chem.Asian J.|15|2879|doi:10.1002/asia.202000579

CCDC 1532856: Experimental Crystal Structure Determination

Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Charles H. Devillers, Dominique Lucas, Jean-Cyrille Hierso|2017|Chem.Commun.|53|6017|doi:10.1039/C7CC02469J

CCDC 939067: Experimental Crystal Structure Determination

Related Article: Guillaume de Robillard, Charles H. Devillers, Doris Kunz, Hélène Cattey, Eric Digard, and Jacques Andrieu|2013|Org.Lett.|15|4410|doi:10.1021/ol401949f

CCDC 1558706: Experimental Crystal Structure Determination

Related Article: Johan Guilbaud, Marine Labonde, Hélène Cattey, Sylvie Contal, Christian Montalbetti, Nadine Pirio, Julien Roger, Jean-Cyrille Hierso|2017|Adv.Synth.Catal.|359|3792|doi:10.1002/adsc.201700858

CCDC 1477185: Experimental Crystal Structure Determination

Related Article: Julien Roger, Sylviane Royer, Hélène Cattey, Aleksandr Savateev, Radomyr V. Smaliy, Aleksandr N. Kostyuk, Jean-Cyrille Hierso|2017|Eur.J.Inorg.Chem.||330|doi:10.1002/ejic.201600502

CCDC 1877101: Experimental Crystal Structure Determination

Related Article: Léa Radal, Petr Vosáhlo, Julien Roger, Hélène Cattey, Régine Amardeil, Ivana Císařová, Petr Štěpnička, Nadine Pirio, Jean‐Cyrille Hierso|2019|Eur.J.Inorg.Chem.||865|doi:10.1002/ejic.201801378

CCDC 1828691: Experimental Crystal Structure Determination

Related Article: Clève D. Mboyi, Delphine Vivier, Ahmad Daher, Paul Fleurat-Lessard, Hélène Cattey, Charles H. Devillers, Claire Bernhard, Franck Denat, Julien Roger, Jean-Cyrille Hierso|2020|Angew.Chem.,Int.Ed.|59|1149|doi:10.1002/anie.201911947

CCDC 1877094: Experimental Crystal Structure Determination

Related Article: Léa Radal, Petr Vosáhlo, Julien Roger, Hélène Cattey, Régine Amardeil, Ivana Císařová, Petr Štěpnička, Nadine Pirio, Jean‐Cyrille Hierso|2019|Eur.J.Inorg.Chem.||865|doi:10.1002/ejic.201801378

CCDC 980178: Experimental Crystal Structure Determination

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CCDC 1983798: Experimental Crystal Structure Determination

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CCDC 1532855: Experimental Crystal Structure Determination

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CCDC 922386: Experimental Crystal Structure Determination

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CCDC 2074193: Experimental Crystal Structure Determination

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CCDC 1559130: Experimental Crystal Structure Determination

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CCDC 943312: Experimental Crystal Structure Determination

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CCDC 1952439: Experimental Crystal Structure Determination

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CCDC 1009245: Experimental Crystal Structure Determination

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CCDC 1054567: Experimental Crystal Structure Determination

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CCDC 1868747: Experimental Crystal Structure Determination

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CCDC 1908611: Experimental Crystal Structure Determination

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CCDC 1983791: Experimental Crystal Structure Determination

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CCDC 1405627: Experimental Crystal Structure Determination

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CCDC 1985140: Experimental Crystal Structure Determination

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CCDC 980174: Experimental Crystal Structure Determination

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CCDC 1908610: Experimental Crystal Structure Determination

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CCDC 980176: Experimental Crystal Structure Determination

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CCDC 1877100: Experimental Crystal Structure Determination

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CCDC 1978287: Experimental Crystal Structure Determination

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CCDC 1908606: Experimental Crystal Structure Determination

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CCDC 1937786: Experimental Crystal Structure Determination

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CCDC 1590300: Experimental Crystal Structure Determination

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CCDC 1983795: Experimental Crystal Structure Determination

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CCDC 1985143: Experimental Crystal Structure Determination

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CCDC 1902394: Experimental Crystal Structure Determination

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CCDC 1433502: Experimental Crystal Structure Determination

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CCDC 1908607: Experimental Crystal Structure Determination

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CCDC 1405168: Experimental Crystal Structure Determination

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CCDC 922385: Experimental Crystal Structure Determination

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CCDC 1828689: Experimental Crystal Structure Determination

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CCDC 1533770: Experimental Crystal Structure Determination

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CCDC 2074196: Experimental Crystal Structure Determination

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CCDC 981911: Experimental Crystal Structure Determination

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CCDC 1433500: Experimental Crystal Structure Determination

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CCDC 1532861: Experimental Crystal Structure Determination

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CCDC 1433507: Experimental Crystal Structure Determination

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CCDC 1405169: Experimental Crystal Structure Determination

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CCDC 1877096: Experimental Crystal Structure Determination

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CCDC 981912: Experimental Crystal Structure Determination

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CCDC 1485961: Experimental Crystal Structure Determination

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CCDC 1559132: Experimental Crystal Structure Determination

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CCDC 943313: Experimental Crystal Structure Determination

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CCDC 1983789: Experimental Crystal Structure Determination

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CCDC 1054565: Experimental Crystal Structure Determination

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CCDC 1902395: Experimental Crystal Structure Determination

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CCDC 1848217: Experimental Crystal Structure Determination

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CCDC 1054566: Experimental Crystal Structure Determination

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CCDC 1532859: Experimental Crystal Structure Determination

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CCDC 981910: Experimental Crystal Structure Determination

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CCDC 1978294: Experimental Crystal Structure Determination

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CCDC 1557314: Experimental Crystal Structure Determination

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CCDC 1985135: Experimental Crystal Structure Determination

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CCDC 2074194: Experimental Crystal Structure Determination

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CCDC 952664: Experimental Crystal Structure Determination

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CCDC 1868750: Experimental Crystal Structure Determination

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CCDC 1985137: Experimental Crystal Structure Determination

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CCDC 1533769: Experimental Crystal Structure Determination

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CCDC 1009243: Experimental Crystal Structure Determination

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CCDC 988196: Experimental Crystal Structure Determination

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CCDC 1985139: Experimental Crystal Structure Determination

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CCDC 1877099: Experimental Crystal Structure Determination

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CCDC 1016993: Experimental Crystal Structure Determination

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CCDC 1559131: Experimental Crystal Structure Determination

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CCDC 943310: Experimental Crystal Structure Determination

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CCDC 980180: Experimental Crystal Structure Determination

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CCDC 1983788: Experimental Crystal Structure Determination

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CCDC 1983796: Experimental Crystal Structure Determination

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CCDC 1474155: Experimental Crystal Structure Determination

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CCDC 1016994: Experimental Crystal Structure Determination

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CCDC 1985134: Experimental Crystal Structure Determination

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CCDC 1813003: Experimental Crystal Structure Determination

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CCDC 1532857: Experimental Crystal Structure Determination

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CCDC 2074195: Experimental Crystal Structure Determination

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CCDC 1983794: Experimental Crystal Structure Determination

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CCDC 1868746: Experimental Crystal Structure Determination

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CCDC 1952440: Experimental Crystal Structure Determination

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