0000000001299829
AUTHOR
Raluca Malacea-kabbara
Modular Hemisyntheses of Boronato- and Trifluoroborato-SubstitutedL-NHBoc Amino Acid and Peptide Derivatives
Modular hemisyntheses of boronato- and trifluoroborato-substituted amino acid and peptide derivatives by using Wittig and C–H iridium-catalyzed borylation as key reactions, are described. Amino ester precursors bearing an aromatic moiety on a lateral chain were prepared by reaction of a new L-NHBoc-amino acid Wittig reagent with the corresponding aromatic aldehydes. After esterification and hydrogenation, the borylation of amino esters was achieved with yields up to 82 % by using the catalysed reaction of bis(pinacolato) diborane reagent (B2Pin2) in the presence of an iridium complex. Interestingly, this iridium-catalyzed borylation was also performed with a dipeptide in 78 % yield. Finally…
P-Chirogenic Triazole-Based Phosphine: Synthesis, Coordination Chemistry, and Asymmetric Catalysis
Phosphonium-Boronate Amino Acid Derivatives as Fluoride Pincers for 18F-Labelling
The synthesis of phosphonium-boronate amino acid derivatives was achieved by quaternization of o-boronatophenylphosphine with iodo-amino acid derivatives. Preliminary radiolabelling studies demonst...
ChemInform Abstract: Efficient Stereoselective Synthesis of Boron L-amino Acid Derivatives Using Wittig and Borylation Reactions
The stereoselective synthesis of a new classes of boronato- or trifluoroborato aminoacids and peptides was described using Wittig and C-H iridium borylation as key reactions. A trifluoroborato-thio...
Efficient Stereoselective Synthesis of Boron L-Amino Acid Derivatives Using Wittig and Borylation Reactions
The stereoselective synthesis of a new classes of boronato- or trifluoroborato aminoacids and peptides was described using Wittig and C-H iridium borylation as key reactions. A trifluoroborato-thio...
o-BF3-Phosphonium pincer moieties in the design of delocalized lipophilic cation based tracers for PET imaging of mitochondrial function
International audience; Objectives: Delocalized lipophilic cations, such as triphenylphosphonium (TPP), are able to cross cell membranes and are known to accumulate in the mitochondria in a membrane potential (MMP) dependent manner. MMP is a reliable indicator of mitochondrial and, consequently, cell and tissue function, hence MMP dependent uptake radiotracers are of interest in cardiac and tumour imaging. Conventional C-18F radiofluorination methods require strict aprotic conditions and heating, moreover, C-18F fluorinated tracers may suffer from metabolic defluorination reducing the quality of the images. The objective of this study was to investigate a suitability of o-B[18F]F3-phosphoni…
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…
Atom Transfer Radical Addition Catalyzed by Ruthenium–Arene Complexes Bearing a Hybrid Phosphine–Diene Ligand
International audience; The synthesis and characterization of a series of arene ruthenium complexes bearing either (3,5-cycloheptadienyl)diphenylphosphine or (cycloheptyl)-diphenylphosphine are reported. Upon irradiation or heating, all these complexes lose their arene ligand but then exhibit a different behavior depending on the nature of the phosphine ligand. (Cycloheptadienyl)phosphine complexes 1 and 3 give a cationic dinuclear Ru complex 5 for which the two Ru atoms are bridged by three chlorido ligands and flanked by two tridendate (cycloheptadienyl)phosphines. (Cycloheptyl)-diphenylphosphine complexes 2 and 4 undergo arene exchange when toluene is used as solvent or degrade in dithlo…
o-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
The synthesis of o-boronato- and o-trifluoroborato-phosphonium salts supported by the L-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from L-serine or L-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato-phosphonium amino esters, respectively. The usefulness of these compounds in peptide cou…
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…
Efficient Synthesis of (P-Chirogenic) o-Boronated Phosphines from sec-Phosphine Boranes
An efficient synthesis of boronated phosphines with an o-phenylene-bridge prepared from sec-phosphine boranes and using benzyne chemistry is reported. Successive reactions of sec-phosphine boranes with n-BuLi and 1,2-dibromobenzene, and then with boron reagents, afford the o-boronatophenylphosphine derivatives in 71% yields. The use of P-chirogenic sec-phosphine boranes leads to the free boronated phosphines with retention of configuration at the P-center after decomplexation. The reaction of P-chirogenic o-boronatophenylphosphine with KHF2 affords the corresponding trifluoroborated phosphine with ee >98%.
ChemInform Abstract: Modular Hemisyntheses of Boronato- and Trifluoroborato-Substituted L-NHBoc Amino Acid and Peptide Derivatives.
Modular hemisyntheses of boronato- and trifluoroborato-substituted amino acid derivatives are achieved based on the reaction of Wittig reagent (I) with aldehydes followed by Ir-catalyzed boronation.
Synthesis of P-Chirogenic Diphosphinotriazoles and Their Use in Asymmetric Catalysis
International audience; The stereoselective synthesis of P-chirogenic diphosphinotriazoles using ephedrine methodology was described. The coordination behavior of these compounds as P,P-ligands has been demonstrated by the preparation as well as the spectroscopic and X-ray crystallographic analyses of a palladium complex. The efficiency of these new P-chirogenic diphosphines in the palladiumcatalyzed asymmetric allylic substitution reaction was also evaluated.
ChemInform Abstract: O-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
The synthesis of o-boronato- and o-trifluoroborato–phosphonium salts supported by the l-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from l-serine or l-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato–phosphonium amino esters, respectively. The usefulness of these compounds in peptide cou…
Designing Silylatedl-Amino Acids using a Wittig Strategy: Synthesis of Peptide Derivatives and18F-Labelling
An efficient semisynthesis of silylated l-amino acids by reaction of silylated benzaldehydes with a phosphonium l-amino acid used as a Wittig reagent is described. The efficiency of the silylated l-amino acids in peptide synthesis was investigated by coupling both the carboxylic acid and the amino moiety with l-alanine and phenylalanine derivatives, respectively. The silylated derivatives were treated with KF or tetrabutylammonium fluoride to give the corresponding fluorosilyl derivatives without racemization. The hydrolysis of the fluorosilylated derivatives in phosphate buffer at pH 7.2 was checked. Finally, the 18F-labelling of di-tert-butylsilylated saturated and unsaturated dipeptides …
CCDC 1868748: 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 1578513: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851
CCDC 1978292: 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 1978293: 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 1578514: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851
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 1953273: Experimental Crystal Structure Determination
Related Article: Jérôme Bayardon, Benjamin Rousselle, Yoann Rousselin, Quentin Bonnin, Raluca Malacea-Kabbara|2020|Eur.J.Org.Chem.|2020|4723|doi:10.1002/ejoc.202000723
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 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 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 1953272: Experimental Crystal Structure Determination
Related Article: Jérôme Bayardon, Benjamin Rousselle, Yoann Rousselin, Quentin Bonnin, Raluca Malacea-Kabbara|2020|Eur.J.Org.Chem.|2020|4723|doi:10.1002/ejoc.202000723
CCDC 1578510: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851
CCDC 1868747: 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 1053706: Experimental Crystal Structure Determination
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167
CCDC 1978287: 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 1937786: 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 1578511: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851
CCDC 1053707: Experimental Crystal Structure Determination
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167
CCDC 1578512: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851
CCDC 1978294: 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 1868750: 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 1053708: Experimental Crystal Structure Determination
Related Article: Jérôme Bayardon , Julie Bernard , Emmanuelle Rémond , Yoann Rousselin , Raluca Malacea-Kabbara , and Sylvain Jugé|2015|Org.Lett.|17|1216|doi:10.1021/acs.orglett.5b00167
CCDC 1868746: 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 1868743: 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 1578509: Experimental Crystal Structure Determination
Related Article: Florian Chotard, Raluca Malacea-Kabbara, Cédric Balan, Ewen Bodio, Michel Picquet, Philippe Richard, Miguel Ponce-Vargas, Paul Fleurat-Lessard, Pierre Le Gendre|2018|Organometallics|37|812|doi:10.1021/acs.organomet.7b00851