Nickel-catalyzed asymmetric transfer hydrogenation of conjugated olefins

被引:69
|
作者
Guo, Siyu [1 ]
Yang, Peng [1 ]
Zhou, Jianrong [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637371, Singapore
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; SUBSTITUTED ACRYLIC-ACIDS; FORMIC-ACID; HOMOGENEOUS HYDROGENATION; LIGANDS; COMPLEXES; ALPHA; REDUCTION; MECHANISM; DEHYDROGENATION;
D O I
10.1039/c5cc01632k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric transfer hydrogenation of electron-deficient olefins is realized with nickel catalysts supported by strongly sigma-donating bisphosphines. Deuterium labeling experiments point to a reaction sequence of formate decarboxylation, asymmetric hydride insertion and non-stereoselective protonation of resulting nickel enolates.
引用
收藏
页码:12115 / 12117
页数:3
相关论文
共 50 条
  • [31] Homogenous nickel-catalyzed chemoselective transfer hydrogenation of functionalized nitroarenes with ammonia-borane
    Dewangan, Chitrarekha
    Kumawat, Sandeep
    Bhatt, Tarun
    Natte, Kishore
    CHEMICAL COMMUNICATIONS, 2023, 59 (99) : 14709 - 14712
  • [32] Ligandless nickel-catalyzed transfer hydrogenation of alkenes and alkynes using water as the hydrogen donor
    Hu, Xiaoping
    Wang, Gaonan
    Qin, Chunxiang
    Xie, Xin
    Zhang, Chunli
    Xu, Wei
    Liu, Yuanhong
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15) : 2619 - 2623
  • [33] Towards a Zinc-Catalyzed Asymmetric Hydrogenation/Transfer Hydrogenation of Imines
    Werkmeister, Svenja
    Fleischer, Steffen
    Junge, Kathrin
    Beller, Matthias
    CHEMISTRY-AN ASIAN JOURNAL, 2012, 7 (11) : 2562 - 2568
  • [34] Iridium-Catalyzed Asymmetric Hydrogenation of Olefins with Chiral N,P and C,N Ligands
    Woodmansee, David H.
    Pfaltz, Andreas
    IRIDIUM CATALYSIS, 2011, 34 : 31 - +
  • [35] Iridium Complex-Catalyzed Transfer Hydrogenation of N-Heteroarenes and Tentative Asymmetric Synthesis
    Ouyang, Lu
    Xia, Yanping
    Liao, Jianhua
    Miao, Rui
    Yang, Xiao
    Luo, Renshi
    ACS OMEGA, 2021, 6 (15): : 10415 - 10427
  • [36] Nickel-catalyzed asymmetric hydrogenation of substituted cinnamic acid esters to synthesize methylsulfonyl-derived phenylalanine
    Ju, Chunzhi
    Wang, Peng
    Kong, Lingkai
    Cai, Jisheng
    Zhang, Guangliang
    Zhang, Suoqin
    NEW JOURNAL OF CHEMISTRY, 2025, 49 (11) : 4446 - 4450
  • [37] Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation
    Chu, Yangyang
    Han, Zhaobin
    Ding, Kuiling
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (06) : 1934 - 1951
  • [38] Nickel-Catalyzed Synthesis of Quinazolinediones
    Beutner, Gregory L.
    Hsiao, Yi
    Razler, Thomas
    Simmons, Eric M.
    Wertjes, William
    ORGANIC LETTERS, 2017, 19 (05) : 1052 - 1055
  • [39] Nickel-Catalyzed Monoarylation of Ammonia
    Borzenko, Andrey
    Rotta-Loria, Nicolas L.
    MacQueen, Preston M.
    Lavoie, Christopher M.
    McDonald, Robert
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (12) : 3773 - 3777
  • [40] Direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids
    Ramachary, Dhevalapally B.
    Sakthidevi, Rajasekar
    Reddy, P. Srinivasa
    RSC ADVANCES, 2013, 3 (32) : 13497 - 13506