Fluorinated Sulfilimino Iminiums: Efficient and Versatile Sources of Perfluoroalkyl Radicals under Photoredox Catalysis.

ABSTRACT

Reported herein is the use of S-perfluoroalkyl sulfilimino iminiums as a new source of RF radicals under visible-light photoredox catalysis (RF =CF3 , C4 F9 , CF2 Br, CFCl2 ). These shelf-stable perfluoroalkyl reagents, readily prepared on gram scale from the corresponding sulfoxide using a one-pot procedure, allow the efficient photoredox-induced oxyperfluoroalkylation of various alkenes using fac-Ir(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.