Copper-Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides

Angew Chem Int Ed Engl. 2018 Nov 19;57(47):15602-15605. doi: 10.1002/anie.201810548. Epub 2018 Oct 30.

Abstract

Secondary or tertiary sulfinamides are prepared by copper-catalyzed transsulfinamidation of primary sulfinamides with O-benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N-aryl sulfinamides with O-benzoyl hydroxylamines under copper catalysis provides N-aryl sulfonimidamides.

Keywords: copper catalysis; sulfinamide; sulfonamide; sulfonimidamide; transsulfinamidation.