Exploiting trans‐Sulfinylation for the Synthesis of Diverse N‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation

Combining simple amines with the bench‐stable sulfinylamine Tr‐NSO allows in situ preparation of reactive alkyl sulfinylamines, which when combined with alkyl radicals generated by photocatalytic decarboxylation, provides N‐alkyl sulfinamides. The reactions are broad in scope and tolerate a wide variety of functional groups on both the acid and amine components. The sulfinamide products are used to prepare a selection of challenging S(VI) products. The method provides a convenient way to use reactive and unstable alkyl sulfinylamines. Trans‐sulfinylation enables the generation of hydrolytically‐sensitive alkyl sulfinylamines in situ from Tr‐NSO and primary amines. We exploit this process alongside alkyl radical generation from carboxylic acids using acridine photocatalysis to prepare a broad selection of N‐alkyl sulfinamides from structurally diverse and readily available feedstocks.