Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis Herein we report a highly efficient method for nickel‐catalyzed C−N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy‐transfer mechanism wherein C−N bond reductive elimination occurs from a triplet excited NiII complex. Late‐stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Angewandte Chemie Wiley

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0044-8249
eISSN
1521-3757
D.O.I.
10.1002/ange.201800699
Publisher site
See Article on Publisher Site

Abstract

Herein we report a highly efficient method for nickel‐catalyzed C−N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy‐transfer mechanism wherein C−N bond reductive elimination occurs from a triplet excited NiII complex. Late‐stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Journal

Angewandte ChemieWiley

Published: Jan 19, 2018

Keywords: ; ; ; ;

References

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