Metal-Free Chemoselective S-Arylation of Sulfenamides To Access Sulfilimines

A novel and efficient S-arylation of sulfenamides with diaryliodonium salts for the synthesis of sulfilimines is developed. The reaction proceeds smoothly under transition-metal-free and air conditions, giving rapid access to sulfilimines in good to excellent yields via selective S-C bond formation. This protocol is scalable and exhibits a broad substrate scope, good functional group tolerance, and excellent chemoselectivity.