Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Taehoon Kim, Stefan J. McCarver, Chulbom Lee, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)3488-3492
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number13
DOIs
StatePublished - Mar 19 2018

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • energy transfer
  • heterocycles
  • nickel
  • photocatalysis
  • sulfonamides

Fingerprint Dive into the research topics of 'Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis'. Together they form a unique fingerprint.

Cite this