Article
Chemistry, Multidisciplinary
Qiang Dai, Lu Liu, Junliang Zhang
Summary: This study successfully achieved the kinetic resolution of rac-secondary phosphine oxides via enantioselective P-benzylation catalysis, delivering both tert- and sec-phosphine oxides in good yield and excellent enantiopurity. The synthetic utilities were further demonstrated by the facile preparation of valuable P-chiral compounds, precursors of bidentate ligands, and transition metal complexes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Anirban Mondal, Niklas O. Thiel, Ruth Dorel, Ben L. Feringa
Summary: The phosphorus stereocentre is crucial in various compounds and efforts are underway to develop stereoselective synthesis methods. Despite advances in metal-catalysed C-P bond formation, generating homochiral phosphorus stereocentres remains challenging. An efficient and flexible method has been presented for the synthesis of various classes of P-chirogenic compounds through functionalization of phosphonamidates with excellent stereoselectivity.
Article
Chemistry, Multidisciplinary
Ying Zhang, Jia Yuan, Guanglong Huang, Hong Yu, Jinpeng Liu, Jian Chen, Sixuan Meng, Jian-Ji Zhong, Li Dang, Guang-Ao Yu, Chi-Ming Che
Summary: Visible-light-induced reactions play an important role in organic synthesis, but efficient photochemical synthesis of enantiomerically pure molecules remains a challenge. This study describes a simple and efficient visible-light-induced reaction for the synthesis of P-chiral heteroaryl phosphine oxides.
Article
Chemistry, Inorganic & Nuclear
Christine Salomon-Bertrand, Jerome Bayardon, Hugo Laureano, Sylvain Juge, Jean-Claude Daran, Maryse Gouygou
Summary: The stereoselective synthesis of new phospholylmethano P-chirogenic-phosphine-borane was achieved by P-C bond formation of the bridge, using electrophilic or nucleophilic P*-building blocks. These ligands behaved as chelating entities towards the cationic rhodium(I) centre, and the resulting chiral rhodium complexes were tested in asymmetric rhodium catalyzed hydrogenation of methyl 2-(acetamido)acrylate.
JOURNAL OF ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Cheng Luan, Chang-Jiang Yang, Lin Liu, Qiang-Shuai Gu, Xin-Yuan Liu
Summary: Transition metal-catalyzed C-P coupling reactions play a significant role in constructing P-stereogenic centers, with the specific stereochemical mechanism depending on the phosphorus starting materials used. Recent developments in asymmetric catalysis have led to efficient kinetic resolution and dynamic kinetic asymmetric C-P coupling of racemic P-stereogenic compounds.
Article
Chemistry, Inorganic & Nuclear
Harish S. Kunchur, Maravanji S. Balakrishna
Summary: The reactions of amide functionalized bisphosphine with platinum salts were studied, resulting in the formation of various complexes. The mechanism of the formation of 1,2-azaphospholene was investigated. Additionally, a palladium complex with low catalyst loading showed excellent catalytic activity in the N-alkylation reaction of amines with alcohols.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Daniel Moser, Kalipada Jana, Christof Sparr
Summary: In this study, the feasibility of atroposelective P-III/P-V=O redox organocatalysis by the Staudinger-aza-Wittig reaction is described. The formation of isoquinoline heterocycles allows for the synthesis of a wide range of valuable atropisomers with high enantioselectivities. The reaction is catalyzed by a chiral phosphine catalyst, with stereocontrol achieved through a silane reductant and Bronsted acid co-catalysis. The products can be easily transformed into N-oxides, naphthol, and triaryl phosphine variants, providing access to diverse aromatic heterocycles with precise control over their configuration.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xingyu Chen, Hongyu Wu, Rongrong Yu, Hong Zhu, Zhiqian Wang
Summary: The palladium-catalyzed C-P bond formation reaction of ArBr/ArOTf using acylphosphines as differential phosphination reagents is reported. The reaction directly affords trivalent phosphines in good yields with a broad substrate scope and functional group tolerance, highlighting the capability of acylphosphines as new phosphorus sources for the direct synthesis of trivalent phosphines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiaoqing Song, Guang Lu, Yi Man, Jing Zhang, Shuo Chen, Chunmiao Han, Hui Xu
Summary: In this study, three carbazole-triphenylphosphine hybrids were designed and synthesized to achieve high efficiency and long lifetime of organic room temperature phosphorescence (RTP). The para-substituted pCzTPP showed high RTP efficiency (>10%) and extended lifetime (>600 ms), surpassing the ortho- and meta- isomers. Theoretical simulation and photophysical investigation revealed that the strong intermolecular p-p and p-p interactions in pCzTPP facilitated the transition probability and triplet stability of (3)pp state, demonstrating the synergy of p-p and p-p in RTP process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jian-Qiu Zhang, Li-Biao Han
Summary: By introducing trimethylsilyl chloride, pentavalent phosphorus compounds can be converted to corresponding intermediates, which can further react with electrophiles or nucleophiles to produce trivalent phosphines efficiently. Chiral phosphines can also be obtained stereospecifically by this strategy.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Julian Loeffler, Viktoria H. Gessner
Summary: Bulky ylide-substituted phosphines have recently been used as effective ligands in homogeneous catalysis. The attempted synthesis of the ylide-substituted fluorenylphosphine resulted in unexpected elimination reactions and the formation of cyclic phosphonium ylide. Coordination to transition metals resulted in the formation of zwitterionic metal complexes with a neutral phosphide ligand.
Article
Chemistry, Organic
Guo-Fu Zhang, Lin-Jun Han, Chen-Fei Guan, Cheng-Rong Ding
Summary: An efficient fluorination strategy for P(O)-H and P(O)-OH compounds using sulfuryl fluoride as the fluorination reagent is reported. This strategy avoids the use of expensive or complex prepreparation reagents for fluoridation and allows for convenient construction of various fluorophosphonates and phosphonofluoridates under mild conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Deqian Peng, Shouzhi Zhang, Wu Fan, Yuan Wen, Suhua Li
Summary: Trifluoromethylphosphines are a rare type of phosphine compound with unique electron-withdrawing properties, resulting in distinctive reactivities. Currently, the structure diversity of TFMPhos products obtained from nucleophilic or electrophilic trifluoromethylation of substrates using phosphine chlorides is very limited and requires one or more steps. In this study, we report a convenient and scalable (up to 100 mmol) method to synthesize diverse trifluoromethylphosphines via direct radical trifluoromethylation of phosphine chlorides with CF(3)Br in the presence of zinc powder.
Article
Chemistry, Physical
Kai -Chun Zhao, Yi-Ying Zhuang, Tian -Hong Jing, Guang-Hui Shi, Lin Guo, Xiao-Li Zhao, Yong Lu, Ye Liu
Summary: Several novel ionic phosphines (L1-L4) with good robustness against water and oxygen were synthesized and characterized. The XPS analysis showed that L1 derived from Xantphos could act as a P, O-hybrid ligand with P, O-chelation to Pd-center. As a result, L1 provided PdCl2(MeCN)2 with high catalytic activity, excellent selectivity, and good stability in the bis-hydroaminocarbonylation of alkynes, yielding N-aryl substituted succinimides with isolated yields of 57-90%. Control experiments and in situ high-pressured FT-IR analysis further confirmed that the studied reaction followed a tandem reaction mechanism involving Pd-H species (m 1942 cm-1) over the L1-Pd(MeCN)2Cl2 catalytic system.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jairus L. Lamola, Paseka T. Moshapo, Cedric W. Holzapfel, Munaka Christopher Maumela
Summary: A new family of biaryl phosphacyclic ligands have been developed for efficient Suzuki-Miyaura cross-coupling of aryl bromides and chlorides, with successful coupling of sterically hindered and heterocyclic substrates at room temperature.
Article
Chemistry, Multidisciplinary
Jerome Bayardon, Yoann Rousselin, Raluca Malacea-Kabbara
Summary: The study describes the stereoselective synthesis of P-chirogenic diphosphinotriazoles using ephedrine methodology, demonstrating their coordination behavior as P,P-ligands through the preparation of a palladium complex and spectroscopic and X-ray crystallographic analyses. The efficiency of these new P-chirogenic diphosphines in the palladium-catalyzed asymmetric allylic substitution reaction was also evaluated.
Article
Chemistry, Medicinal
Benjamin Rousselle, Aurelie Massot, Malorie Privat, Lucile Dondaine, Audrey Trommenschlager, Florence Bouyer, Jerome Bayardon, Francois Ghiringhelli, Ali Bettaieb, Christine Goze, Catherine Paul, Raluca Malacea-Kabbara, Ewen Bodio
Summary: A phosphine gold(I) and phosphine-phosphonium gold(I) complexes with a fluorescent coumarin moiety were synthesized. The complexes exhibited interesting photophysical properties and demonstrated moderate to strong antiproliferative activity.
Article
Chemistry, Multidisciplinary
Emmanuelle Remond, Jean-Alain Fehrentz, Laure Lienart, Sebastien Clement, Jean-Louis Baneres, Florine Cavelier
Summary: The study demonstrates a new method of synthesizing fluorescent P-hydroxybinaphtylphosphole-oxide or -sulfide for labeling biomolecules, particularly for characterizing GHSR ligands.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Inorganic & Nuclear
Valentin Vaillant-Coindard, Benjamin Theron, Gael Printz, Florian Chotard, Cedric Balan, Yoann Rousselin, Philippe Richard, Iogann Tolbatov, Paul Fleurat-Lessard, Ewen Bodio, Raluca Malacea-Kabbara, Jerome Bayardon, Samuel Dagorne, Pierre Le Gendre
Summary: This study investigated the replacement of imine functionality in phenoxy-imine (FI) ligands with a more robust N,N,N'-trisubstituted amidine function, resulting in the synthesis of new phenoxy-amidine (FA) ligands. The structures of the synthesized ligands and complexes were determined using X-ray diffraction and NMR spectroscopy. These complexes exhibited excellent catalytic performance in the ring-opening polymerization of rac-lactide, with high tolerance to the presence of lactic acid.
Article
Chemistry, Inorganic & Nuclear
Amlia Godard, Laura Abad Galan, Jean Rouillon, Shaymaa Al Shehimy, Wassima Tajani, Charlotte Cave, Raluca Malacea-Kabbara, Yoann Rousselin, Pierre Le Gendre, Arnaud Fihey, Mohamed Bendellaa, Benoit Busser, Lucie Sancey, Boris Le Guennic, Christophe Bucher, Olivier Maury, Christine Goze, Ewen Bodio
Summary: Aza-boron-dipyrromethenes (Aza-BODIPYs) are a class of fluorophores with azadipyrromethene (aza-DIPY) ligand rigidified by a boron atom. Complexes of group 13 metals (aluminum and gallium) were synthesized and their properties were investigated. AzaGaDIPY and azaAlDIPY exhibited significant red-shifted fluorescence compared to aza-BODIPY, making them promising for optical medical imaging.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Pawel Jewula, Mickael Grandmougin, Melanie Choppin, Anna Maria Chiara Tivelli, Agnese Amati, Yoann Rousselin, Lydia Karmazin, Jean-Claude Chambron, Michel Meyer
Summary: Six- and seven-membered cyclic hydroxamic acids are commonly found in siderophores and can act as terminal binding units. However, the coordination chemistry of these ligands with Fe3+, the target metal ion of siderophores, has not been previously investigated. In this study, four complexes were synthesized and studied, and X-ray diffraction analysis showed that the AZEPO(-) complexes had better minimized interligand repulsion energies and shorter Fe-O bond distances compared to the PIPO complexes.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Valentin Vaillant-Coindard, Florian Chotard, Benjamin Theron, Cedric Balan, Jerome Bayardon, Raluca Malacea-Kabbara, Ewen Bodio, Yoann Rousselin, Paul Fleurat-Lessard, Pierre Le Gendre
Summary: Ethylene- and phenylene-bridged bis-(salicylamidine) ligands can be easily synthesized from ethylene or phenylenediamine and iminium chloride derivatives. These complexes show catalytic activity in the controlled ring-opening polymerization of rac-lactide to generate poly(lactic acid) with slight isotactic bias.
INORGANIC CHEMISTRY
(2023)
Article
Agriculture, Multidisciplinary
Luigi Clerat, Emmanuelle Remond, Remi Schneider, Florine Cavelier, Eric Vives
Summary: Varietal thiols contribute to the aroma of various wines and beers, and their production depends on the metabolism of non-odorant aroma precursors by yeast. The conversion of these precursors is limited, so the use of exogenous carbon-sulfur beta-lyase (CSL) enzyme from Lactobacillus delbrueckii subsp. bulgaricus was explored to enhance the conversion. The study investigated the activity of the enzyme on different precursors, its behavior in the presence of competing analogues and at different pH values, and provided insights for substrate recognition, paving the way for aroma release in beer and wine.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sacha Bodin, Santo Previti, Emmanuelle Jestin, Delphine Vimont, Imade Ait-Arsa, Frederic Lamare, Emmanuelle Remond, Elif Hindie, Florine Cavelier, Clement Morgat
Summary: This study describes the development of a radiometalated neurotensin analogue (JMV 7488) targeting NTS2. The results demonstrate that JMV 7488 has high hydrophilicity, strong affinity and selectivity for NTS2, and can induce internalization in cells. In vivo experiments showed significant uptake of [68Ga]Ga-JMV 7488 in tumor tissue.
Article
Chemistry, Inorganic & Nuclear
Benjamin Theron, Valentin Vaillant-Coindard, Cedric Balan, Yoann Rousselin, Jerome Bayardon, Raluca Malacea-Kabbara, Pierre Le Gendre
Summary: This study reports the synthesis of a new generation of phenoxy-amidine ligands with an ortho-N-linked trisubstituted amidine. Mono- or bis-ligated complexes were obtained from the reaction of phenol-amidine proligands with aluminum and zinc alkyls depending on the metal/ligand ratio. The solid-state structure of these complexes was determined by X-Ray diffraction analysis. The Zn complexes with a phenoxy-amidine ligand featuring an additional dimethylamino arm showed the best performance in the ring-opening polymerization of rac-lactide.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Sacha Bodin, Santo Previti, Emmanuelle Jestin, Delphine Vimont, Imade Ait-Arsa, Emmanuelle Remond, Elif Hindie, Florine Cavelier, Clement Morgat, Frederic Lamare
Summary: This study describes the radiometalated neurotensin analogue JMV 7488 targeting NTS2. It shows good hydrophilicity and affinity towards NTS2, as well as significant tumor uptake in biodistribution studies.
Article
Crystallography
Michael Knorr, Lydie Viau, Yoann Rousselin, Marek M. Kubicki
Summary: The study identified a polymeric compound named CP1, formed from the reaction of CuBr and THT in MeCN solution. CP1 consists of two-dimensional layers interconnected by bridging THT ligands, forming a three-dimensional supramolecular network in the crystal.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Ali Sanda Bawa, Rita Meunier-Prest, Yoann Rousselin, Jean-Pierre Couvercelle, Christine Stern, Bernard Malezieux, Marcel Bouvet
Summary: A series of charge transfer complexes (CTCs) were successfully formed using solvent-free processing techniques in a simple confined environment, with systematic studies conducted on crystals using Raman spectroscopy. Additionally, three new crystalline structures were obtained, each exhibiting unique molecular arrangements and interaction patterns.
Article
Crystallography
Yoann Rousselin, Sylvie Yolka, Alexandre Clavel
Summary: Two polymorphs of (S)-{2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl} 2,2-dimethylpropanethioate, C26H38O5S, have been identified, with the molecules connected via hydrogen bonds in different directions.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
(2021)
Article
Chemistry, Inorganic & Nuclear
Benjamin Rousselle, Florence Bouyer, Jerome Bayardon, Myriam Laly, Francois Ghiringhelli, Yoann Rousselin, Ewen Bodio, Raluca Malacea-Kabbara
Summary: A family of gold(I)-phosphonium-phosphine complexes with enhanced anti-proliferative properties was successfully synthesized through an efficient synthetic strategy. These complexes showed superior efficacy compared to clinically used anticancer drugs, indicating their potential for further development in cancer treatment.
DALTON TRANSACTIONS
(2021)
