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

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.