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. 2023 Jan 27;25(3):533-537.
doi: 10.1021/acs.orglett.2c04278. Epub 2023 Jan 13.

Copper-Catalyzed Hydroamination of gem-Difluoroalkenes Access to Diversified α-Difluoromethyl Amines

Dachang Bai  1   2 , Yuanyuan Guo  1 , Dandan Ma  1 , Xiuli Guo  1 , Hao Wu  1
Affiliations

Copper-Catalyzed Hydroamination of gem-Difluoroalkenes Access to Diversified α-Difluoromethyl Amines

Dachang Bai et al. Org Lett. .

Abstract

The difluoromethyl group (CF2H) is of great importance in medicinal chemistry. We report herein an efficient method for the synthesis of diversified α-difluoromethyl amines through copper-catalyzed hydroamination of gem-difluoroalkenes, where the C-N bond formed via a α-CF2H transition-metal intermediate. This new reaction proceeds through Cu-H insertion to gem-difluoroalkenes and gives valuable alkyl-CF2H-containing compounds, which overcome the much more challenged β-F elimination from α-fluoroalkyl organocopper species. The reaction exhibits broad substrate scope with readily available starting materials and commercial catalysis.

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