1143-92-6Relevant articles and documents
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Sidgwick,Thomas,Sutton
, p. 406 (1933)
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Dehalogenative Cross-Coupling of gem-Difluoroalkenes with Alkyl Halides via a Silyl Radical-Mediated Process
Tian, Hao,Yang, Shaoxiang,Wang, Xiaochen,Xu, Wentao,Liu, Yuxiu,Li, Yongqiang,Wang, Qingmin
, p. 12772 - 12782 (2021/09/13)
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.
Trifluoromethylation and Monofluoroalkenylation of Alkenes through Radical–Radical Cross-Coupling
Wang, Qiang,Qu, Yi,Tian, Hao,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
, p. 8686 - 8690 (2019/06/17)
The first visible-light-induced trifluoromethylation and monofluoroalkenylation of simple alkenes via a challenging radical–radical cross-coupling step was achieved. This method provided a mild, step-economical and redox-neutral route to privileged two different fluorinated difunctionalized allyl compounds. The utility of this method is illustrated by late-stage modification of medically important molecules.