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Copper-Catalyzed, Aerobic Synthesis of <i>N</i>H-Sulfonimidamides from Primary Sulfinamides and Secondary Amines

Peng Wu, Joachim Demaerel, Deshen Kong, Ding Ma, Carsten Bolm

2022Organic Letters19 citationsDOIOpen Access PDF

Abstract

H-Sulfonimidamides are prepared by copper-catalyzed coupling of primary sulfinamides with secondary amines. Neither a ligand nor an additive is needed, and air is the terminal oxidant. The reactions occur at room temperature, show good functional group tolerance, and lead to products in good yields. A sulfanenitrile is proposed as an intermediate in this oxidative amination.

Topics & Concepts

ChemistryAminationPrimary (astronomy)CatalysisCopperFunctional groupLigand (biochemistry)Combinatorial chemistryOrganic chemistryPolymer chemistryReceptorBiochemistryPhysicsAstronomyPolymerSynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods