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Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis
Author(s) -
Kim Taehoon,
McCarver Stefan J.,
Lee Chulbom,
MacMillan David W. C.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201800699
Subject(s) - aryl , electrophile , chemistry , sulfonamide , combinatorial chemistry , nickel , catalysis , reductive elimination , halide , drug discovery , photoredox catalysis , aryl halide , photochemistry , stereochemistry , organic chemistry , biochemistry , alkyl , photocatalysis
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 Ni II complex. Late‐stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.