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

Marion Daniel (1) , Guillaume Dagousset (1) , Patrick Diter (1) , Pierre-André Klein , Beátrice Tuccio (2) , Anne-Marie Goncalves (1) , Géraldine Masson (3) , Emmanuel Magnier (1)

1 ILV - Institut Lavoisier de Versailles
2 ICR - Institut de Chimie Radicalaire
3 ICSN - Institut de Chimie des Substances Naturelles

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.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry

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, 2017, ⟨10.1002/anie.201700290⟩. ⟨hal-02113752⟩