Addition of Organometallic Reagents to an Episulfoxide Delivers Sulfenate Anions: Modular Synthesis of Sulfoxides and Sulfinamides

Reported herein is the application of a sterically hindered episulfoxide for the modular synthesis of sulfoxides and sulfinamides. SO transfer from the episulfoxide to Grignard or organolithium reagents (RMgX or RLi) generates sulfenate anions (RSO^-), which serve as versatile intermediates in subsequent S-C or S-N bond-forming reactions.