Base-Promoted S-Arylation of Sulfenamides for the Synthesis of Sulfilimines

Org Lett. 2023 Jun 16;25(23):4335-4339. doi: 10.1021/acs.orglett.3c01436. Epub 2023 Jun 2.

Abstract

Sulfilimines are key intermediates to common motifs in medicines and agrochemicals. Typically, this class of compounds are prepared by imidation of thioethers, transition-metal-catalyzed or base-promoted sulfur alkylation and transition-metal-catalyzed sulfur arylation. Here, we report a practical and efficient base-mediated sulfur arylation reaction for the preparation of sulfilimines. A wide range of N-acyl and N-aryl sulfenamides react with various diaryliodonium salts smoothly to afford the sulfilimines in high yields with excellent chemoselectivities.

MeSH terms

  • Catalysis
  • Molecular Structure
  • Transition Elements*

Substances

  • sulfenamide
  • sulfilimine
  • Transition Elements