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A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes.

ABSTRACT: A 4-tetrafluoropyridinylthio group was suggested as a new photoredox-active moiety. The group can be directly installed on difluorostyrenes in a single step by the thiolene click reaction. It proceeds upon visible light catalysis with 9-phenylacridine providing various difluorinated sulfides as radical precursors. Single electron reduction of the C-S bond with the formation of fluoroalkyl radicals is enabled by the electron-poor azine ring. The intermediate difluorinated sulfides were involved in a series of photoredox reactions with silyl enol ethers, alkenes, nitrones and an alkenyl trifluoroborate.

SUBMITTER: Zubkov MO

PROVIDER: S-EPMC8146146 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes.

Zubkov Mikhail O MO Kosobokov Mikhail D MD Levin Vitalij V VV Kokorekin Vladimir A VA Korlyukov Alexander A AA Hu Jinbo J Dilman Alexander D AD

Chemical science 20191126 3

A 4-tetrafluoropyridinylthio group was suggested as a new photoredox-active moiety. The group can be directly installed on difluorostyrenes in a single step by the thiolene click reaction. It proceeds upon visible light catalysis with 9-phenylacridine providing various difluorinated sulfides as radical precursors. Single electron reduction of the C-S bond with the formation of fluoroalkyl radicals is enabled by the electron-poor azine ring. The intermediate difluorinated sulfides were involved i ...[more]

PMID: 34123046

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