Enantioselective nickel-catalyzed electrochemical reductive conjugate alkenylation of α,β-unsaturated ketones

被引:0
|
作者
Somprasong, Siriphong [1 ]
Wan, Bin [1 ]
Harutyunyan, Syuzanna R. [1 ]
机构
[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 3, NL-9747 AG Groningen, Netherlands
基金
欧洲研究理事会;
关键词
ASYMMETRIC 1,4-ADDITION; ORGANONICKEL COMPLEXES; ALKENYLBORONIC ACIDS; ARYL; ADDITIONS; ALKENES; ALPHA; REAGENTS; ELECTROLYSIS; ALKYLATION;
D O I
10.1039/d4sc06891b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic electrochemical asymmetric catalysis is emerging as a promising strategy for the synthesis of chiral compounds. Herein, we report an asymmetric electrochemical nickel-catalysed reductive conjugate addition of alkenyl bromides/aryl iodides to alpha,beta-unsaturated ketones in an undivided cell, leading to addition products with high yields and excellent enantioselectivities (up to 96% yield and 96% ee).
引用
收藏
页码:802 / 808
页数:7
相关论文
共 50 条
  • [1] Enantioselective Reductive Conjugate Alkenylation of α,β-Unsaturated Ketones and Amides via Nickel Catalysis
    Zhao, Mengxin
    Zhang, Luoqiang
    Zhou, Jianrong Steve
    ACS CATALYSIS, 2024, 14 (08) : 6228 - 6235
  • [2] Nickel-Catalyzed Enantioselective Reductive Arylation of Common Ketones
    Huang, Shuai
    Zhou, Jianrong Steve
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (19) : 12895 - 12900
  • [3] Nickel-catalyzed enantioselective reductive amination of benzylic ketones in alcohols
    Xiuhua Wang
    Jianrong Steve Zhou
    Science China(Chemistry), 2024, 67 (08) : 2566 - 2570
  • [4] Nickel-catalyzed enantioselective reductive amination of benzylic ketones in alcohols
    Wang, Xiuhua
    Zhou, Jianrong Steve
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (08) : 2566 - 2570
  • [5] Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide
    Yang, Peng
    Lim, Li Hui
    Chuanprasit, Pratanphorn
    Hirao, Hajime
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 12083 - 12087
  • [6] Nickel-Catalyzed Stereoselective Alkenylation of Ketones Mediated by Hydrazine
    Xia, Shumei
    Cao, Dawei
    Zeng, Huiying
    He, Liang-Nian
    Li, Chao-Jun
    JACS AU, 2022, 2 (08): : 1929 - 1934
  • [7] Enantioselective nickel-catalyzed reductive dicarbofunctionalization of olefins
    Anthony, David
    Diao, Tianning
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [8] Acid-Catalyzed Direct Conjugate Alkenylation of α,β-Unsaturated Ketones
    Okamoto, Kazuhiro
    Tamura, Eisuke
    Ohe, Kouichi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (40) : 10639 - 10643
  • [9] Nickel-Catalyzed Cycloaddition of α,β,γ,δ-Unsaturated Ketones with Alkynes
    Horie, Hiroaki
    Kurahashi, Takuya
    Matsubara, Seijiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) : 8956 - 8959
  • [10] NICKEL-CATALYZED CONJUGATE ADDITION OF ALKYNYL GROUPS TO ALPHA-BETA-UNSATURATED KETONES
    SCHWARTZ, J
    CARR, DB
    HANSEN, RT
    DAYRIT, FM
    JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15): : 3053 - 3061