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Sulfonyl chlorides are inexpensive reactants extensively explored for functionalization, but never considered for radical hydrosulfonylation of alkenes. Herein, we report that tris(trimethylsilyl)silane is an ideal hydrogen atom donor enabling highly effective photoredox-catalyzed hydrosulfonylation of electron-deficient alkenes with sulfonyl chlorides. To increase the generality of this transformation, polarity-reversal catalysis (PRC) was successfully implemented for alkenes bearing alkyl substituents. This late-stage functionalization method tolerates a remarkably wide range of functional groups, is operationally simple, scalable, and allows access to building blocks which are important for medicinal chemistry and drug discovery.

Original publication

DOI

10.1002/anie.202004070

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

06/07/2020

Volume

59

Pages

11620 - 11626

Keywords

alkenes, hydrosulfonylation, photochemistry, radicals, sulfonyl chlorides