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

Sulfiliminesare key intermediates to common motifs in medicinesand agrochemicals. Typically, this class of compounds are preparedby imidation of thioethers, transition-metal-catalyzed or base-promotedsulfur alkylation and transition-metal-catalyzed sulfur arylation.Here, we report a practical and efficient base-mediated sulfur arylationreaction for the preparation of sulfilimines. A wide range of N-acyl and N-aryl sulfenamides react withvarious diaryliodonium salts smoothly to afford the sulfilimines inhigh yields with excellent chemoselectivities.

Automated summary

This article presents a practical and efficient base-mediated sulfur arylation reaction for the preparation of sulfilimines. By using various N-acyl and N-aryl sulfenamides, and diaryliodonium salts as reactants, the sulfilimines can be obtained in high yields with excellent chemoselectivities.