C-H Bond Arylation of Pyrazoles at the β-Position: General Conditions and Computational Elucidation for a High Regioselectivity

International audience; Direct arylation of most five-membered ring heterocycles are generally easily accessible and strongly favored at the α-position using classical palladium-catalysis. Conversely, regioselective functionalization of such heterocycles at the concurrent β-position remains currently very challenging. Herein, we report general conditions for regioselective direct arylation at the β-position of pyrazoles, while C-H α-position is free. By using aryl bromides as the aryl source and a judicious choice of solvent, the arylation reaction of variously N-substituted pyrazoles simply proceeds via β-C-H bond functionalization. The β-regioselectivity is promoted by a ligand-free palla…

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…

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.

Cover Feature: Palladium‐Catalyzed Electrophilic C–H‐Bond Fluorination: Mechanistic Overview and Supporting Evidence (Eur. J. Org. Chem. 2‐3/2019)

Phosphine Ligands Based on the Ferrocenyl Platform: Advances in Catalytic Cross-Couplings

Ferrocenyl skeletons tagged with a variety of donor atoms (metalloligands) have become popular in modern metal-catalyzed organic transformations, broadening the applications. Ferrocenylphosphines, such as 1′-bis(diphenylphosphino)ferrocene (dppf), have been widely used as metalloligands in academic and industrial research, motivating further investigation into novel ferrocenylphosphine ligands. The current review concentrated non-exhaustively on emblematic applications of different ferrocenylphosphine ligands in transition metal-catalyzed cross-coupling strategies. Initially, the stereochemical aspects of the ferrocenyl skeleton, nomenclature, and applications of chiral ferrocenyl phosphine…

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…

Ortho -Functionalized Aryltetrazines by Direct Palladium-Catalyzed C−H Halogenation: Application to Fast Electrophilic Fluorination Reactions

International audience; A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precurso…

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…

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…

Ambident electrophilicity of 4‐nitrobenzochalcogenadiazoles: Kinetic studies and structure‐reactivity relationships

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…

Synthesis and Catalytic Use of Polar Phosphinoferrocene Amidosulfonates Bearing Bulky Substituents at the Ferrocene Backbone

International audience; Anionic phosphinoferrocene amidosulfonates bearing sterically demanding t-butyl substituents in positions 3 and 3' of the ferrocene scaffold, viz. rac-(Et3NH)[Fe(η5-tBuC5H3PR2)(η5-tBuC5H3C(O)NHCH2SO3)] (R = phenyl and cyclohexyl) were synthesized by amidation of the corresponding phosphinocarboxylic acids, [Fe(η5-tBuC5H3PR2)(η5-tBuC5H3CO2H)]. These ditopic polar phosphinoferrocenes and their non-t-butylated analogues have been used as lig-ands to prepare zwitterionic (η3-allyl)palladium(II) complexes [Pd(η3-C3H5){Fe(η5-R'C5H3PR2)(η5-R'C5H3C(O)NHCH2SO3)}] (R' = H, tBu, R = Ph, Cy). Depending on the isolation procedure and crystallization condi-tions, some complexes we…

ChemInform Abstract: Palladium-Polypyrrole Nanocomposites Pd@PPy for Direct C-H Functionalization of Pyrroles and Imidazoles with Bromoarenes.

Palladium–polypyrrole nanocomposites (Pd@PPy) with unique combination of high palladium dispersion (nanoparticle size 2.4 nm) and high palladium content (35 wt%) are efficient catalysts for the selective arylation of substituted pyrroles and imidazoles with either activated or deactivated aryl bromides. The performances of the recoverable supported palladium catalyst matches the best performances of homogeneous systems based on Pd(OAc)2 at 0.5–0.2 mol%, and largely overwhelm the classical Pd/C catalyst.

Phenol Derivatives in Ruthenium-Catalyzed C-H Arylation: A General Synthetic Access to Azole-Based Congested Polyaromatics

The Hydrogen‐Storage Challenge: Nanoparticles for Metal‐Catalyzed Ammonia Borane Dehydrogenation

International audience; Dihydrogen is one of the sustainable energy vectors envisioned for the future. However, the rapidly reversible and secure storage of large quantities of hydrogen is still a technological and scientific challenge. In this context, this review proposes a recent state-of-the-art on H 2 production capacities from the dehydrogenation reaction of ammonia borane (and selected related amine-boranes) as a safer solid-source of H 2 by hydrolysis (or solvolysis), according to the different developed nanoparticle-based catalysts. The review groups the results according to the transition metals constituting the catalyst according a special view to current cost/availability consid…

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,…

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.

Space and Light, Towards an Interactive Simulation of Lighting

International audience; Une image est une vue, à un instant donné, de l'équilibre lumineux présent dans une scène. Cet équilibre résulte d'un système complexe où l'énergie provenant des sources est re-distribuée dans l'espace par les matériaux appliqués aux formes. Si cet équilibre est perturbé par une modification des conditions lumineuses, l'image précédente n'est plus valide. En cela elle ne représente qu'un instant d'un lieu et non le lieu lui même. Nous proposons ici une approche pour la simulation interactive de l'éclairage dans une scène complexe. Une application à cette étude étant la production d'images vivantes et confondantes dans le cadre de la réalité augmentée.

Palladium C–N bond formation catalysed by air-stable robust polydentate ferrocenylphosphines: a comparative study for the efficient and selective coupling of aniline derivatives to dichloroarene

The arylation of aniline derivatives with dichloroarenes under a low palladium content (below the currently used 5 to 10 mol%) was studied using nine different ferrocenylphosphine ligands, including the easily accessible 1,1′-bis(diphenylphosphino)ferrocene, DPPF. The electron-enriched air-stable tridentate ferrocenylpolyphosphine 1,2-bis(diphenylphosphino)-1′-(diisopropylphosphino)-4-tert-butylferrocene, L5, employed in 2 mol% in combination with 1 mol% [PdCl(η3-C3H5)]2 allows an efficient and selective coupling, while such demanding substrates currently induce chloroarene homocoupling and/or dehalogenation processes. The scope and limitation of the optimized system are explored, with a fo…

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.

Palladium-Catalysed CH Bond Electrophilic Fluorination of Highly Substituted Arylpyrazoles: Experimental and DFT Mechanistic Insights

A general protocol for palladium-catalysed CH mono- and di-fluorination of highly substituted arylpyrazoles is reported. Coupling pathways and substrate limitations are discussed in the light of complementary mechanistic experimental and density functional theory (DFT) studies. The mono- and di-ortho-fluorination of arylpyrazoles having substituted pyrazole groups and ortho-, meta-, or para-substituted arene moieties is achieved. Various pyrazole groups can efficiently promote the direct CH activation/fluorination of substrates bearing valuable reactive ester, cyano, halide and nitro functions. The presence of methoxy, methyl and trifluoromethyl is tolerated on the pyrazole directing groups…

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…

Direct arylation of heterocycles: the performances of ferrocene-based polyphosphane ligands in palladium-catalyzed C-H bond activation

International audience; The palladium-catalyzed direct arylation of alkylated- furan, thiophene, and thiazole and benzoxazole heterocycles with electronically and sterically deactivated bromoarenes was selectively and efficiently promoted by ferrocenyl polyphosphanes. In this C[BOND]H bond activation reaction of heteroaromatics, the performances of polydentate di-, tri-, and tetraphosphane ligands were compared, showing that the triphosphane 1,1′,2-tris(diphenylphosphino)-4-tert-butylferrocene 3 was the most effective for the coupling. The introduction of more electron-donating (iPr) or electron-withdrawing (furyl) groups on the phosphorus atoms did not improve the ligand performances. The …

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.

Nanocatalysts for High Selectivity Enyne Cyclization: Oxidative Surface Reorganization of Gold Sub-2-nm Nanoparticle Networks

International audience; Ultrasmall gold nanoparticles (NPs) stabilized in networks by polymantane ligands (diamondoids) were successfully used as precatalysts for highly selective heterogeneous gold-catalyzed dimethyl allyl(propargyl)malonate cyclization to 5-membered conjugated diene. Such reaction usually suffers from selectivity issues with homogeneous catalysts. This control over selectivity further opened the way to one-pot cascade reaction, as illustrated by the 1,6-enyne cycloisomerization–Diels–Alder reaction of dimethyl allyl propargyl malonate with maleic anhydride. The ability to assemble nanoparticles with controllable sizes and shapes within networks concerns research in sensor…

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.

Gold(I) Complexes of Ferrocenyl Polyphosphines: Aurophilic Gold Chloride Formation and Phosphine-Concerted Shuttling of a Dinuclear [ClAu···AuCl] Fragment

International audience; A smart steric control of the metallocene backbone in bis- and poly(phosphino)ferrocene ligands favors intramolecular aurophilic interactions between [AuCl] fragments in polynuclear gold(I) complexes. We synthesized and characterized by multinuclear NMR and X-ray diffraction analysis mono-, di-, and polynuclear gold complexes of constrained ferrocenyl diphosphines, which bear either bulky tert-butyl groups or more flexible siloxane substituents at the cyclopentadienyl rings. The complexes meso-1,1'-bis-(diphenylphosphino)-3,3'-di-tert-butylferrocene (4-m), rac-1,1'-bis[bis-(5-methy1-2-furyl)phosphino]-3,3'-di-tert-butyfferrocene (5-r), and rac-1,1'-bis ( diphenylphos…

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…

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…

ChemInform Abstract: ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions.

A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to …

Palladium‐Catalyzed Electrophilic C–H‐Bond Fluorination: Mechanistic Overview and Supporting Evidence

International audience; Palladium-catalyzed electrophilic fluorination is a particularly attractive and challenging synthetic issue. Because of the rapid evolution of this topic, a critical point on the mechanistic and experimental advances is provided herein. In the present review, we focused on current mechanistic understanding in electrophilic fluorination (and related halogenations) catalyzed by palladium, mainly with N-directing group. Our discussion is based on the well-characterized or calculated pertinent metal species and intermediates used for analyzing the plausible catalytic cycles. A particular effort has been devoted to gathering supporting data for the putative species involv…

C–H Halogenation of Pyridyl Sulfides Avoiding the Sulfur Oxidation: A Direct Catalytic Access to Sulfanyl Polyhalides and Polyaromatics

Palladium-catalyzed oxidative C–H halogenation and acetoxylation reactions of S-unprotected sulfides, selectively directed by pyridinyl groups, allows the formation of C–X bonds (X = I, Br, Cl, OAc) by using simple halosuccinimide or phenyliodine diacetate (PIDA) oxidants. The undesired formation of sulfoxides and/or sulfones, which are usually observed under oxidative conditions, is fully obviated. Under the solvent-dependent conditions that we proposed, sulfide C–H functionalization is achieved in less than 1 h without any direct electrophilic halogenation at the pyridine moiety. N-Directed ortho-C–H activation of aryl also facilitates dibromination reactions which are hardly accessible w…

Palladium–Polypyrrole Nanocomposites Pd@PPy for Direct C–H Functionalization of Pyrroles and Imidazoles with Bromoarenes

International audience; Palladium–polypyrrole nanocomposites (Pd@PPy) with unique combination of high palladium dispersion (nanoparticle size 2.4 nm) and high palladium content (35 wt%) are efficient catalysts for the selective arylation of substituted pyrroles and imidazoles with either activated or deactivated aryl bromides. The performances of the recoverable supported palladium catalyst matches the best performances of homogeneous systems based on Pd(OAc)2 at 0.5–0.2 mol%, and largely overwhelm the classical Pd/C catalyst.

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…

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…

Solvent-free ruthenium-catalysed triflate coupling as a convenient method for selective azole-o-C-H monoarylation.

Metal-catalysed ortho-directed C–H functionalization usually faces selectivity issues in the competition between mono- and disubstitution processes. We report herein the ruthenium-catalysed N-directed C–H monoarylation of arylpyrazoles with a selectivity of up to 96% or that generally reaches values above 80%. This selectivity is an effect of solvent-free conditions associated with sulfonate reagents, in the absence of frequently used acidic additives.

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…

CCDC 1433505: 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 1983790: Experimental Crystal Structure Determination

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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

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CCDC 1433497: Experimental Crystal Structure Determination

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CCDC 1908608: Experimental Crystal Structure Determination

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CCDC 1908609: Experimental Crystal Structure Determination

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CCDC 1433499: Experimental Crystal Structure Determination

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CCDC 1919134: Experimental Crystal Structure Determination

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CCDC 1877098: Experimental Crystal Structure Determination

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CCDC 1485963: Experimental Crystal Structure Determination

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CCDC 1919135: Experimental Crystal Structure Determination

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CCDC 1532860: Experimental Crystal Structure Determination

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CCDC 980179: Experimental Crystal Structure Determination

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CCDC 980175: Experimental Crystal Structure Determination

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CCDC 1828690: Experimental Crystal Structure Determination

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CCDC 1557313: Experimental Crystal Structure Determination

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CCDC 2077804: Experimental Crystal Structure Determination

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CCDC 1433506: Experimental Crystal Structure Determination

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CCDC 1433503: Experimental Crystal Structure Determination

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CCDC 1433501: Experimental Crystal Structure Determination

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CCDC 1433498: Experimental Crystal Structure Determination

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CCDC 2089400: Experimental Crystal Structure Determination

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CCDC 1983787: Experimental Crystal Structure Determination

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CCDC 1433504: Experimental Crystal Structure Determination

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CCDC 1405174: Experimental Crystal Structure Determination

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CCDC 1877102: Experimental Crystal Structure Determination

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CCDC 1532862: Experimental Crystal Structure Determination

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CCDC 2089403: Experimental Crystal Structure Determination

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CCDC 1993888: Experimental Crystal Structure Determination

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CCDC 1405175: Experimental Crystal Structure Determination

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CCDC 1009630: Experimental Crystal Structure Determination

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CCDC 1438419: Experimental Crystal Structure Determination

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CCDC 1009631: Experimental Crystal Structure Determination

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CCDC 1908612: Experimental Crystal Structure Determination

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CCDC 2109009: Experimental Crystal Structure Determination

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CCDC 1485958: Experimental Crystal Structure Determination

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CCDC 1991440: Experimental Crystal Structure Determination

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CCDC 1877097: Experimental Crystal Structure Determination

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CCDC 980177: Experimental Crystal Structure Determination

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CCDC 1983797: Experimental Crystal Structure Determination

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CCDC 1532856: Experimental Crystal Structure Determination

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CCDC 1558706: Experimental Crystal Structure Determination

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CCDC 1477185: Experimental Crystal Structure Determination

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CCDC 1877101: Experimental Crystal Structure Determination

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CCDC 2077807: Experimental Crystal Structure Determination

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CCDC 1828691: Experimental Crystal Structure Determination

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CCDC 1405170: Experimental Crystal Structure Determination

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CCDC 1877094: Experimental Crystal Structure Determination

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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 2074193: Experimental Crystal Structure Determination

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CCDC 1559130: Experimental Crystal Structure Determination

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CCDC 1952439: Experimental Crystal Structure Determination

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CCDC 2089401: 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 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 1438417: Experimental Crystal Structure Determination

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CCDC 1908606: Experimental Crystal Structure Determination

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CCDC 2089402: Experimental Crystal Structure Determination

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CCDC 2077806: Experimental Crystal Structure Determination

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CCDC 2089404: Experimental Crystal Structure Determination

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CCDC 1983795: 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 1828689: Experimental Crystal Structure Determination

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CCDC 2074196: Experimental Crystal Structure Determination

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CCDC 1433500: Experimental Crystal Structure Determination

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CCDC 2077802: 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 1009629: 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 2089399: 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 1983789: Experimental Crystal Structure Determination

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CCDC 1902395: Experimental Crystal Structure Determination

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CCDC 1532859: Experimental Crystal Structure Determination

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CCDC 1438418: Experimental Crystal Structure Determination

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CCDC 1557314: Experimental Crystal Structure Determination

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CCDC 2074194: Experimental Crystal Structure Determination

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CCDC 1877099: Experimental Crystal Structure Determination

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CCDC 1559131: Experimental Crystal Structure Determination

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CCDC 2077801: 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 1813003: Experimental Crystal Structure Determination

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CCDC 1532857: Experimental Crystal Structure Determination

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CCDC 1983794: Experimental Crystal Structure Determination

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CCDC 1952440: Experimental Crystal Structure Determination

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CCDC 1983793: Experimental Crystal Structure Determination

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CCDC 2077803: Experimental Crystal Structure Determination

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CCDC 2077805: Experimental Crystal Structure Determination

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CCDC 1485959: Experimental Crystal Structure Determination

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CCDC 1877095: Experimental Crystal Structure Determination

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CCDC 1983785: Experimental Crystal Structure Determination

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CCDC 1485960: Experimental Crystal Structure Determination

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CCDC 980181: Experimental Crystal Structure Determination

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CCDC 2089405: Experimental Crystal Structure Determination

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CCDC 1433508: Experimental Crystal Structure Determination

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CCDC 1405171: Experimental Crystal Structure Determination

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CCDC 1983792: Experimental Crystal Structure Determination

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CCDC 1485962: Experimental Crystal Structure Determination

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CCDC 1983786: Experimental Crystal Structure Determination

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