Reagent-controlled Selective Synthesis of Sulfinamides and Sulfoximines from tert-Butanesulfinamide

The preparation of optically pure sulfinamides from tert-butanesulfinamide previously involved multi-step sequences, including the incorporation of desired chemical fragments to and subsequent removal of tert-butyl group from the sulfur center. We disclose a step-economic method herein that can accomplish these transformations in a single reaction. The formal ^tBu-to-Ar exchange reaction of tert-butanesulfinamide is achieved using aryldiazonium reagents and copper catalyst. The catalyst and additives are crucial for the success of this method. Alternatively, slight modification to reaction conditions results in the formation of tert-butanesulfoximines, which are likely the transient precursors of ^tBu-to-Ar exchange to give sulfinamides via in situ debutylation.