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Hydrosulfonylation of alkenes with sulfonyl chlorides under visible light activation

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.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1002/anie.202004070

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Inorganic Chemistry
Role:
Author


Publisher:
Wiley
Journal:
Angewandte Chemie International Edition More from this journal
Volume:
59
Issue:
28
Pages:
11620-11626
Publication date:
2020-04-14
Acceptance date:
2020-04-14
DOI:
EISSN:
1521-3773
ISSN:
1433-7851


Language:
English
Keywords:
Pubs id:
1100659
Local pid:
pubs:1100659
Deposit date:
2020-04-18

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