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Issue 3, 2020
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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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Supplementary files

Article information


Submitted
13 Sep 2019
Accepted
25 Nov 2019
First published
26 Nov 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 737-741
Article type
Edge Article

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, 11, 737
DOI: 10.1039/C9SC04643G

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