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

Organic & Biomolecular Chemistry Pub Date: 2019-10-17 DOI: 10.1039/C9OB02119A

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.

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