Pd-catalyzed C–N coupling of vinylbromides and sulfonimidamides: a facile synthesis of N′-vinylsulfonimidamides

Abstract

N′-Vinyl sulfonimidamides have been synthesized through a Pd-catalyzed C–N cross coupling between the N′-(imine nitrogen) of N′-deprotected sulfonimidamides and vinyl bromides. The hitherto unreported products were obtained in moderate to excellent yield, and the C–C double bond geometry of the vinylic substrates were retained during the course of reaction. Single crystal X-ray crystallographic analysis confirmed the product structure. Furthermore, we demonstrate that the formed N′-vinyl sulfonimidamides could undergo hydrogenation with Pd–C/H₂ to provide N′-alkyl sulfonimidamides.