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

Chemical Science
Mikhail O ZubkovAlexander D Dilman

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.

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Citations

Jul 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Dmitry L LipilinAlexander D Dilman
Jun 20, 2020·Beilstein Journal of Organic Chemistry·Stephanie G E AmosJerome Waser
Jul 18, 2020·Chemical Communications : Chem Comm·Mikhail D KosobokovAlexander D Dilman
Dec 22, 2020·Chemical Communications : Chem Comm·Vitalij V Levin, Alexander D Dilman
Mar 31, 2021·The Journal of Organic Chemistry·Denise E SunagawaSensuke Ogoshi
May 1, 2021·Organic Letters·Liubov I Panferova, Alexander D Dilman
Nov 5, 2020·Angewandte Chemie·Liubov I PanferovaAlexander D Dilman

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