posted on 2021-08-30, 12:04authored byHao Tian, Shaoxiang Yang, Xiaochen Wang, Wentao Xu, Yuxiu Liu, Yongqiang Li, Qingmin Wang
Herein,
we describe a convenient general protocol for monofluoroalkenylation
reactions of alkyl bromides involving cooperative visible-light photoredox
catalysis and halogen abstraction. Mechanistic experiments showed
that the products were generated by selective cross-coupling of aliphatic
radicals with fluoroalkenyl radicals. Silyl radical-mediated halogen
abstraction enabled the protocol to be used for the monofluoroalkenylation
of a broad range of alkyl and heteroaryl halides. The protocol could
be carried out on a gram scale and was applied to cholesterol, indicating
its utility for late-stage monofluoroalkenylation reactions.