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Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

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.

SUBMITTER: Kim T

PROVIDER: S-EPMC5937270 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

Kim Taehoon T McCarver Stefan J SJ Lee Chulbom C MacMillan David W C DWC

Angewandte Chemie (International ed. in English) 20180227 13

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<sup>II</sup> complex. Late-stage sulfonamidation in the synthesis of a pharmacologi ...[more]

PMID: 29424956

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