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Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation
Author(s) -
Hell Sandrine M.,
Meyer Claudio F.,
Misale Antonio,
Sap Jeroen B. I.,
Christensen Kirsten E.,
Willis Michael C.,
Trabanco Andrés A.,
Gouverneur Véronique
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004070
Subject(s) - sulfonyl , chemistry , surface modification , catalysis , combinatorial chemistry , photoredox catalysis , trimethylsilyl , alkyl , silane , organic chemistry , photochemistry , photocatalysis
Abstract 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.