Profiling the oxidative activation of DMSO-F6 by pulse radiolysis and translational potential for radical C–H trifluoromethylation

Abstract

The oxidative activation of the perfluorinated analogue of dimethyl sulfoxide, DMSO-F₆, by hydroxyl radicals efficiently produces trifluoromethyl radicals based on pulse radiolysis, laboratory scale experiments, and comparison of rates of reaction for analogous radical systems. In comparison to commercially available precursors, DMSO-F₆ proved to be more stable, easier to handle and overall more convenient than leading F₃C-reagents and may therefore be an ideal surrogate to study F₃C radicals for time-resolved kinetics studies. In addition, we present an improved protocol for the preparation of this largely unexplored reagent.