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

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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.

Graphical abstract: A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes

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Publication details

The article was received on 13 Sep 2019, accepted on 25 Nov 2019 and first published on 26 Nov 2019


Article type: Edge Article
DOI: 10.1039/C9SC04643G
Chem. Sci., 2020, Advance Article
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    A novel photoredox-active group for the generation of fluorinated radicals from difluorostyrenes

    M. O. Zubkov, M. D. Kosobokov, Vitalij V. Levin, V. A. Kokorekin, A. A. Korlyukov, J. Hu and A. D. Dilman, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC04643G

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