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

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.