Auto-Tandem Copper-Catalyzed Carboxylation of Undirected Alkenyl C-H Bonds with CO₂ by Harnessing β-Hydride Elimination

Harekrishna Sahoo, Liang Zhang*, Jianhua Cheng, Masayoshi Nishiura and Zhaomin Hou*

*Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan, Email: lzhangriken.jp, houzriken.jp

H. Sahoo, L. Zhang, J. Cheng, M. Nishiura, Z. Hou, J. Am. Chem. Soc., 2022, 144, 23585-23594.

DOI: 10.1021/jacs.2c10754

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Abstract

A tandem borylation/carboxylation of C-H bonds in two mechanistically distinct catalytic cycles enables a carboxylation of alkenyl C-H bonds with CO₂ in the presence of B₂pin₂. In this transformation, β-hydride elimination of an alkyl copper intermediate is facilitated, while its reaction with CO₂ is suppressed.

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proposed mechanism

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Key Words

carboxylation

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ID: J48-Y2022