Citation: Chen Si, Zhao Yanchuan. C(sp³)—C(sp³) Bond Formation via Transition-Metal Mediated and Catalyzed Reductive Homocouplings[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3078-3093. doi: 10.6023/cjoc202005072 shu

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

Chen Si ^a ,
Zhao Yanchuan ^a,b,,

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

Corresponding author: Zhao Yanchuan, zhaoyanchuan@sioc.ac.cn
Received Date: 26 May 2020
Revised Date: 19 July 2020
Available Online: 30 July 2020
Fund Project: the National Natural Science Foundation of China 21421002Project 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)the Strategic Priority Research Program of the Chinese Academy of Sciences XDC 06020102the National Natural Science Foundation of China 91956120the National Natural Science Foundation of China 21871291

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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.
- C(sp³)-C(sp³) bond formation,
- reductive homocoupling,
- transition-metal catalysis,
- photoredox catalysis,
- total synthesis
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沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

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