Ligand-Enabled Copper-Catalyzed Ullmann-Type S–C Bond Formation to Access Sulfilimines

A copper-catalyzed Ullmann-type cross-coupling reaction of sulfenamides with aryl iodides is developed. The key to success is the use of a 2-methylnaphthalen-1-amine-derived amide ligand, which enables the formation of an S-C bond to access functionalized sulfilimines in good to excellent yields at room temperature. This method has the advantages of mild conditions, a broad substrate scope, good functional group compatibility, and high chemoselectivity. The utility of this protocol is highlighted through late-stage modification of drug-relevant molecules and sulfilimine product derivatization.