Review
Chemistry, Inorganic & Nuclear
Jessica Margalef, Maria Biosca, Pol de la Cruz Sanchez, Jorge Faiges, Oscar Pamies, Montserrat Dieguez
Summary: The success of phosphine-oxazoline ligands has led to advancements in P-oxazoline ligand families, resulting in diverse structures and more efficient ligands for asymmetric transformations. Through proper design, these heterodonor bidentate ligand families exhibit superior catalytic performance in a variety of asymmetric reactions.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Organic
Tushar Janardan Pawar, Liliette Barcelona-Cazanave, Israel Bonilla-Landa, Magdalena Escobar, J. Oscar C. Jimenez-Halla, Alma Altuzar-Molina, Patricia Romero-Arellano, Andrew J. F. Edmunds, Martin Aluja, Jose Luis Olivares-Romero
Summary: This study presents a highly efficient iridium-catalyzed asymmetric hydrogenation approach for the total synthesis of biologically active (R,L) A. ludens host marking pheromone (HMP). The use of a novel Ir(i)-complex and a chiral P,N-ligand resulted in excellent enantioselectivities of up to 94% ee. The streamlined synthetic route involving seven reaction steps offers improved efficiency and shorter synthesis timelines compared to previous methods.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Yulong Zhang, Peichao Zhao, Shengnan Sun, Qian Wu, Enxue Shi, Junhua Xiao
Summary: The authors developed a camphor-derived 2,3-diol as a chiral template to synthesize diverse P(III) and P(V) chiral compounds, which are highly desirable for asymmetric catalysis in organic chemistry.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Juana M. Perez, Roxana Postolache, Marta Castineira Reis, Esther G. Sinnema, Denisa Vargova, Folkert de Vries, Edwin Otten, Luo Ge, Syuzanna R. Harutyunyan
Summary: Chiral Mn(I) complexes have been shown to activate H-P bonds, providing a general method for the hydrophosphination of internal and terminal alpha,beta-unsaturated nitriles. Metal-ligand cooperation, a previously unconsidered strategy for catalytic H-P bond activation, plays a key role in the mechanistic action of the Mn(I)-based catalyst. Computational studies support a stepwise mechanism for the hydrophosphination reaction and offer insights into the origin of enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Applied
Yin-Feng Ma, Chuan-Jin Hou, De-Quan Wei, Xinwei He, Ting-Ting Chu, Xiu-shuai Chen, Xiang-Ping Hu
Summary: The asymmetric hydrogenation of beta-ketophosphonates with chiral Ir/P,N,N-ligands catalyst leads to high yields of beta-hydroxyphosphonates with good or excellent enantioselectivities under mild conditions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Adrian Garcia-Zaragoza, Christian Cerezo-Navarrete, Andres Mollar-Cuni, Pascual Ona-Burgos, Jose A. Mata, Avelino Corma, Luis M. Martinez-Prieto
Summary: The catalytic properties of graphene-supported ruthenium nanoparticles have been adjusted by modifying their metal surface with pyrene-tagged N-heterocyclic-carbene ligands. The activity and selectivity of the catalyst are highly dependent on the surface coverage of the ligands, with higher coverage leading to lower activity but higher selectivity. The reactivity and stability of the catalysts can be controlled by modifying the surface with specific ligands.
CATALYSIS SCIENCE & TECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Yong Yuan, Xue Liu, Jingcheng Hu, Pengjie Wang, Shengchun Wang, Hesham Alhumade, Aiwen Lei
Summary: In this study, a facile and novel electrochemical method was developed for the synthesis of tertiary phosphines with excellent yields. The protocol showed good reaction selectivity and scalability.
Article
Chemistry, Multidisciplinary
Chenghao Li, Shu-Xin Zhang, Yu Feng, Yan-Mei He, Qing-Hua Fan
Summary: The chiral ruthenium-catalyzed enantioselective hydrogenation of tetrapyridine-type N-heteroarenes was developed for the first time. The adjacent tetraheteroaromatic substrates showed high reactivity, enantioselectivity, and diastereoselectivity, with yields up to 93%, enantiomeric excess (>99% ee), and diastereomeric ratio of 92:8, respectively, in the presence of phosphine-free chiral cationic ruthenium diamine complexes. The potential application of chiral tetradentate pyridine-amine products as chiral ligands was demonstrated in the Cu-catalyzed asymmetric Friedel-Crafts alkylation reaction between indoles and nitroalkenes.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Bram B. C. Peters, Norman Birke, Luca Massaro, Pher G. Andersson
Summary: The catalytic asymmetric hydrogenation of olefins is a powerful method for synthesizing chiral compounds. By using an iridium N,P-complex catalyst, various prochiral unsaturated amides can be efficiently reduced with high enantioselectivities. The attractive features of this method include its application in the synthesis of fenpropidin and the potential use of isomeric mixtures as starting materials.
Article
Chemistry, Organic
Yin-Bo Wan, Xiang-Ping Hu
Summary: A readily available and highly modular class of chiral P,N,N-ligands have been developed and successfully applied in the Ir-catalyzed asymmetric hydrogenation. These ligands exhibited excellent activity, enantioselectivity, and substrate tolerance, thus providing optically active compounds with high yields and enantioselectivities. This study demonstrates the utility of these ligands in diverse product transformation and the synthesis of biologically active compounds.
Article
Chemistry, Multidisciplinary
Niklas F. Both, Anke Spannenberg, Haijun Jiao, Kathrin Junge, Matthias Beller
Summary: The use of bis(NHC) manganese(I) complexes 3 as catalysts for the hydrogenation of esters was investigated. Various aromatic and aliphatic esters were successfully hydrogenated at mild temperatures and low catalyst loadings using complexes 3 with KHBEt3 as additive, highlighting the efficiency of the novel catalytic system. Additionally, the versatility of the developed catalytic system was demonstrated by the hydrogenation of other substrate classes like ketones, nitriles, N-heteroarenes, and alkenes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Maria Biosca, Pol de la Cruz-Sanchez, Daniel Tarr, Patricia Llanes, Erik A. Karlsson, Jessica Margalef, Oscar Pamies, Miquel A. Pericas, Montserrat Dieguez
Summary: A chiral phosphine-triazole ligand has been developed for the Ir-catalyzed asymmetric hydrogenation of exocyclic benzofused alkenes, which overcomes previous limitations and exhibits excellent enantioselectivity. The catalyst shows good tolerance towards various substituents and substitution patterns at both aromatic rings, making it an effective tool for hydrogenation of exocyclic olefins.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Pep Rojo, Agusti Lledos, Antoni Riera, Xavier Verdaguer
Summary: A threonine-derived phosphine-oxazoline iridium catalyst with excellent selectivity in the hydrogenation of N-Boc-2,3-diarylallylamines is reported. The reversible cyclometallation process and the influence of substitution at the phenyl group of the oxazoline on this equilibrium are thoroughly investigated. X-Ray analysis reveals the coordination mode of the cyclometallated tridentate ligand. Furthermore, the utilization of Ir(III) pre-catalysts or Ir(I)/Ir(III) mixtures in hydrogenation reactions is proposed based on the observed equilibrium dynamics.
Article
Chemistry, Inorganic & Nuclear
Lingyu Kong, Yajie Chou, Muriel Albalat, Marion Jean, Nicolas Vanthuyne, Stephane Humbel, Paola Nava, Herve Clavier
Summary: The concept of atropisomeric N-heterocyclic carbene (NHC)-metal complexes with C-2-symmetry was extended to palladium-based complexes. Through a comprehensive study of NHC precursors and screening of various NHC ligands, the formation of meso complexes was successfully circumvented. Eight atropisomeric NHC-palladium complexes were prepared and obtained with high enantiopurities through efficient chiral HPLC resolution. These complexes demonstrated good activity in the intramolecular alpha-arylation of amides, leading to the isolation of cyclic products with excellent enantioselectivities (up to 98% ee).
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Bao-De Ma, Sheng-Hua Du, Yu Wang, Xiao-Ming Ou, Ming-Zhi Huang, Li-Xin Wang, Xiao-Guang Wang
TETRAHEDRON-ASYMMETRY
(2017)
Article
Chemistry, Organic
Tingting Miao, Baode Ma, Ziyuan Ding, Youran Liu, Yan-Mei He, Qing-Hua Fan
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Multidisciplinary
Ma Baode, Deng Guojun, Liu Ji, He Yanmei, Fan Qinghua
ACTA CHIMICA SINICA
(2013)
Article
Chemistry, Multidisciplinary
Baode Ma, Tingting Miao, Yihua Sun, Yanmei He, Ji Liu, Yu Feng, Hui Chen, Qing-Hua Fan
CHEMISTRY-A EUROPEAN JOURNAL
(2014)
Article
Chemistry, Multidisciplinary
Yong Li, Baode Ma, Yanmei He, Feng Zhang, Qing-Hua Fan
CHEMISTRY-AN ASIAN JOURNAL
(2010)
Article
Chemistry, Organic
Ji Liu, Yu Feng, Baode Ma, Yan-Mei He, Qing-Hua Fan
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Inorganic & Nuclear
Ji Liu, Baode Ma, Yu Feng, Yanmei He, Qing-Hua Fan
INORGANICA CHIMICA ACTA
(2014)
Article
Chemistry, Multidisciplinary
Hongyan Zhang, Baode Ma, Faxu Lin, Zhiyong Yang, Guangxi Huang, Bing Shi Li, Ben Zhong Tang
Summary: This study presents a method to screen reported compounds for stimuli-responsive properties and discover new reversible fluorescence properties, successfully identifying compound 1 with reversible tricolored mechanoluminescence and recyclability, suitable for optical recording and anti-counterfeiting applications.
MATERIALS CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Chao Wu, Jiang Wang, Xumu Zhang, Runtong Zhang, Baode Ma
Summary: Novel ferrocene-based PNN ligands were prepared and found to be highly effective catalysts for the homogeneous hydrogenation of cyclic imides with iridium (TON up to 50,000). The hydrogenation mode could be finely tuned by tiny changes in the ligands, leading to high yields of a variety of omega-hydroxylactams and omega-hydroxyamides with different functional groups.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Liu Ji, Ma Baode, Yang Nianfa, Fan Qinghua
PROGRESS IN CHEMISTRY
(2010)
