Access to gem-Difluoroalkenes via Organic Photoredox-Catalyzed gem-Difluoroallylation of Alkyl Iodides

Songlin Yan, Weijie Yu, Jianye Zhang, Hongmei Fan, Zhifeng Lu, Zhenming Zhang* and Tao Wang*

*College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, Jiangxi 330022, P.R. China, zxm6272126.com, wangtaojxnu.edu.cn

S. Yan, W. Yu, J. Zhang, H. Fan, Z. Lu, Z. Zhang, T. Wang, J. Org. Chem., 2022, 87, 1574-1584.

DOI: 10.1021/acs.joc.1c02659

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Abstract

An organic photoredox-catalyzed gem-difluoroallylation of α-trifluoromethyl alkenes with alkyl iodides provides gem-difluoroalkene derivatives via C-F bond cleavage. This transition-metal-free transformation utilizes a readily available organic dye (4CzIPN) as the sole photocatalyst and N,N,N',N'-tetramethylethylenediamine as the radical activator.

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proposed reaction pathway

4CzIPN

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Key Words

allylation, gem-difluoroalkenes, photochemistry, organocatalysis

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ID: J42-Y2022