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Photocatalyzed Defluorinative Dichloromethylation of α-CF 3 Alkenes Using CHCl 3 as the Radical Source.

Mei-Chun WuYi-Xuan ChenMing-Zhi LiJun-An XiaoZhi-Peng YeJian-Ping GuanHao-Yue XiangKai ChenJun-An Xiao
Published in: The Journal of organic chemistry (2022)
A visible-light-induced defluorinative dichloromethylation of α-CF 3 alkenes was developed with cheap and readily accessible chloroform simultaneously as a dichloromethylation reagent and reaction medium, leading to the facile preparation of new polyhalogenated scaffolds. Notably, the change from CHCl 3 to CDCl 3 offers a straightforward pathway for accessing the deuterated analogues with excellent degrees of D incorporation. Mechanistic studies suggested the reaction underwent a radical addition of the dichloromethyl radical with alkenes, followed by sequential single-electron transfer and defluorination. This protocol features mild conditions, easy operation, facile scalability, and high efficiency, allowing convenient access to dichloronated gem -difluoroalkenes.
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