Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (10): 3078-3093.DOI: 10.6023/cjoc202005072 Previous Articles     Next Articles

Special Issue: 黄乃正院士七十华诞专辑


陈思a, 赵延川a,b   

  1. a 中国科学院上海有机化学研究所 中国科学院有机氟化学重点实验室 上海 200032;
    b 中国科学院上海有机化学研究所 中国科学院能量调控材料重点实验室 上海 200032
  • 收稿日期:2020-05-26 修回日期:2020-07-19 发布日期:2020-08-01
  • 通讯作者: 赵延川
  • 基金资助:
    国家自然科学基金(Nos.21421002,21871291,91956120)、中国科学院战略性先导科技专项(No.XDC 06020102)资助项目.

C(sp3)—C(sp3) Bond Formation via Transition-Metal Mediated and Catalyzed Reductive Homocouplings

Chen Sia, Zhao Yanchuana,b   

  1. a CAS Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    b CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2020-05-26 Revised:2020-07-19 Published:2020-08-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21421002, 21871291, 91956120), and the Strategic Priority Research Program of the Chinese Academy of Sciences (No. XDC 06020102).

C(sp3)-C(sp3) bond coupling is of great significance in organic synthesis, among which reductive homocoupling has showed its special superiority in construction of symmetrical molecular structures. These reactions are usually operationally simple, which utilize organohalides as substrates, avoiding the handling of highly reactive organometallic reagents. The use of non-precise metals as the catalyst makes reductive homocouplings amenable for large-scale synthesis. Improved efficiency and selectivity have been observed in systems involving photoredox catalytic processes, ionic-liquids, and inorganic nanomaterials. This review aims to summarize the development of reductive couplings. In this review, various reductive homocouplings are summarized, where transition metals, such as cobalt, nickel, copper, titanium, and rhodium are involved. Photo-mediated reductive couplings are then highlighted followed by a discussion on applications of reductive couplings in natural products synthesis and polymer sciences.

Key words: C(sp3)-C(sp3) bond formation, reductive homocoupling, transition-metal catalysis, photoredox catalysis, total synthesis