Exploiting <i>trans</i>‐Sulfinylation for the Synthesis of Diverse <i>N</i>‐Alkyl Sulfinamides via Decarboxylative Sulfinamidation
Jonathan A. Andrews, Russell G. Woodger, Christopher F. Palmer, Darren L. Poole, Michael C. Willis
Abstract
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.
Topics & Concepts
AlkylChemistryStereochemistryOrganic chemistrySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods