Hydrosulfonylation of Alkenes with Sulfonyl Chlorides under Visible Light Activation

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-07, Vol.59 (28), p.11620-11626
Main Authors: Hell, Sandrine M., Meyer, Claudio F., Misale, Antonio, Sap, Jeroen B. I., Christensen, Kirsten E., Willis, Michael C., Trabanco, Andrés A., Gouverneur, Véronique
Format: Article
Language:English
Subjects:
Alkenes
Catalysis
Chlorides
Functional groups
hydrosulfonylation
photochemistry
Polarity
radicals
sulfonyl chlorides
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Summary: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. Radical new approach: Sulfonyl chlorides have been applied in the radical hydrosulfonylation of alkenes. 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 was successfully implemented for alkenes bearing alkyl substituents.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202004070