Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

被引:8
作者
Gale-Day, Zachary J. [1 ]
机构
[1] Univ Calif San Francisco, Chem & Chem Biol, 675 Nelson Rising Ln, San Francisco, CA 94158 USA
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 05期
关键词
electrochemistry; nickel; copper; reduction; cross-coupling; sp(2)-sp(3); ALKYL-HALIDES; ARYL HALIDES; MECHANISTIC ASPECTS; NICKEL CATALYSIS; BROMIDES; REDUCTION; AMINATION; ZINC; DERIVATIVES; STRATEGIES;
D O I
10.1055/s-0040-1706085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Traditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp(2) electrophiles and nucleophiles with sp(3) coupling partners to form both C-C and C-heteroatom bonds. 1 Introduction 2 Nickel-Catalyzed C-C sp(2)-sp(3) Coupling Reactions 3 Coupling of Aryl Groups with Heteroatomic Nuclei 4 Conclusion
引用
收藏
页码:879 / 888
页数:10
相关论文
共 50 条
  • [1] Recent Advances of Transition Metal-Catalyzed C(sp3)-C(sp3) Cross-Coupling Reactions of Non-activated Alkyl Halides
    Zhang, Wenman
    Dai, Jianjun
    Xu, Huajian
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (09) : 1820 - 1833
  • [2] Nickel-Catalyzed Electrochemical C(sp3)-C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
    Luo, Jian
    Hu, Bo
    Wu, Wenda
    Hu, Maowei
    Liu, T. Leo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 6107 - 6116
  • [3] Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds
    Li, Yaqiong
    Fan, Yuhang
    Jia, Qianfa
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 350 - 362
  • [4] Recent Advances in C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formation through Cathodic Reactions: Reductive and Convergent Paired Electrolyses
    Claraz, Aurelie
    Masson, Geraldine
    ACS ORGANIC & INORGANIC AU, 2022, 2 (02): : 126 - 147
  • [5] Electrochemical NiH-Catalyzed C(sp3)-C(sp3) Coupling of Alkyl Halides and Alkyl Alkenes
    Li, Pengfei
    Kou, Guangsheng
    Feng, Tian
    Wang, Minyan
    Qiu, Youai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (44)
  • [6] Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides
    Hofmayer, Maximilian S.
    Hammann, Jeffrey M.
    Cahiez, Gerard
    Knochel, Paul
    SYNLETT, 2018, 29 (01) : 65 - 70
  • [7] Metal-Catalyzed C(sp2)-N Bond Formation
    Correa, Arkaitz
    Bolm, Carsten
    AMINATION AND FORMATION OF SP2 C-N BONDS, 2013, 46 : 55 - 85
  • [8] Recent progress in metal-catalyzed C(sp3)-P bond formation
    Tu, Jia-Lin
    Shen, Zhengjia
    Huang, Binbin
    TETRAHEDRON, 2024, 168
  • [9] Metal-Catalyzed Ionic Decarboxylative Cross-Coupling Reactions of C(sp3) Acids: Reaction Development, Mechanisms, and Application
    Moon, Patrick J.
    Lundgren, Rylan J.
    ACS CATALYSIS, 2020, 10 (03) : 1742 - 1753
  • [10] Metal-catalyzed reactions for the C(sp2)-N bond formation: achievements of recent years
    Beletskaya, Irina P.
    Averin, Alexei D.
    RUSSIAN CHEMICAL REVIEWS, 2021, 90 (11) : 1359 - 1396