Citation: Wenwen Cui, Yu Li, Xufeng Li, Junxin Li, Xiuyan Song, Jian Lv, Yuan-Ye Jiang, Daoshan Yang. Rapid formation of Csp³–Csp³ bonds through copper-catalyzed decarboxylative Csp³–H functionalization[J]. Chinese Chemical Letters, ;2023, 34(1): 107477. doi: 10.1016/j.cclet.2022.04.075 shu

Rapid formation of Csp³–Csp³ bonds through copper-catalyzed decarboxylative Csp³–H functionalization

Wenwen Cui ^{a, 1} ,
Yu Li ^{b, 1} ,
Xufeng Li ^c ,
Junxin Li ^a ,
Xiuyan Song ^a ,
Jian Lv ^a ,
Yuan-Ye Jiang ^{b, *,} ,
Daoshan Yang ^{a, d, *,}

a.
Key Laboratory of Optic-Electric Sensing and Analytical Chemistry for Life Science, MOE, College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
b.
School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China
c.
Zhejiang Wansheng Co., Ltd., Linhai 317000, China
d.
Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China

yangdaoshan@tsinghua.org.cn

yuanyejiang@qfnu.edu.cn

Received Date: 28 February 2022
Revised Date: 26 April 2022
Accepted Date: 28 April 2022
Available Online: 1 May 2022

Figures(9)

Transition-metal-catalyzed decarboxylative and CH functionalization strategy for the construction of Csp²-Csp², Csp²-Csp, and Csp²-Csp³ bonds has been extensively studied. However, research surveys of this synthetic strategy for the Csp³-Csp³ bond forming reactions are surprisingly scarce. Herein, we present an efficient approach for the rapid formation of Csp³–Csp³ bond through copper-catalyzed decarboxylative Csp³–H functionalization. The present method should provide a useful access to C3-substituted indole scaffolds with possible biological activities. Mechanistic experiments and DFT calculations supported a dual-Cu(Ⅱ)-catalytic cycle involving rate-determining decarboxylation in an outer-sphere radical pathway and spin-crossover-promoted CC bond formation. This strategy offers a promising synthesis method for the construction of Csp³–Csp³ bond in the field of synthetic and pharmaceutical chemistry and extends the number of still limited copper-catalyzed decarboxylative Csp³–Csp³ bond forming reaction.
- Copper,
- Cross-coupling,
- Csp³-H functionaliztion,
- Decarboxylation,
- Csp³–Csp³ bond formation
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沈阳化工大学材料科学与工程学院沈阳 110142

Rapid formation of Csp3–Csp3 bonds through copper-catalyzed decarboxylative Csp3–H functionalization

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通讯作者: 陈斌, bchen63@163.com

Rapid formation of Csp³–Csp³ bonds through copper-catalyzed decarboxylative Csp³–H functionalization