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Fluorinated sulfilimino iminiums: a versatile source of perfluoroalkyl radicals under photoredox catalysis

Marion Daniel 1 Guillaume Dagousset 1 Patrick Diter 2 Pierre-André Klein Beátrice Tuccio 3 Anne-Marie Goncalves 1 Géraldine Masson 4 Emmanuel Magnier 1
1 ILV - Institut Lavoisier de Versailles
2 UMR 8180
3 ICR - Institut de Chimie Radicalaire
4 ICSN - Institut de Chimie des Substances Naturelles
Abstract : Reported herein is the use of S-perfluoroalkyl sulfilimino iminiums as anew source of RF radicals under visible-light photoredox catalysis (RF=CF3,C4F9,CF2Br, CFCl2). These shelf-stable perfluoroalkyl reagents,readily prepared on gram scale from the corresponding sulfoxide using aone-pot procedure,allowthe efficient photoredoxinduced oxyperfluoroalkylation of various alkenes using facIr(ppy)3 as the photocatalyst. Importantly,spin-trapping/electron paramagnetic resonance experiments were carried out to characterize all the radical intermediates involved in this radical/cationic process.
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https://hal-amu.archives-ouvertes.fr/hal-02113752
Contributor : Béatrice Tuccio <>
Submitted on : Monday, April 29, 2019 - 10:27:43 AM
Last modification on : Saturday, July 3, 2021 - 12:26:29 AM

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Marion Daniel, Guillaume Dagousset, Patrick Diter, Pierre-André Klein, Beátrice Tuccio, et al.. Fluorinated sulfilimino iminiums: a versatile source of perfluoroalkyl radicals under photoredox catalysis. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2017, ⟨10.1002/anie.201700290⟩. ⟨hal-02113752⟩

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