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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202004070
Subject(s) - sulfonyl , chemistry , surface modification , photoredox catalysis , catalysis , combinatorial chemistry , trimethylsilyl , alkyl , silane , organic chemistry , photochemistry , photocatalysis
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.