Ni-Catalyzed Photochemial Sulfamidation of Aryl Chlorides with Soluble Organic Amine as Base

Abstract

Transition-metal-catalyzed sulfonamidation is an attractive approach for the synthesis of N-(hetero)aryl sulfonamides, which are present in many bioactive pharmaceuticals. However, most catalyst systems require the use of strongly basic alkoxide salts as base, which leads to problems of functional group compatibility and a lack of selectivity for sulfonamides containing multiple NH 2 groups. Here, we reported the Ni-catalyzed photochemical C−N coupling of (hetero)aryl chlorides with sulfonamides using mild organic amines as base without the addition of external photocatalyst. This Ni-catalyzed C−N coupling features a broad substrate scope (84 examples), excellent functional group tolerance, and high sulfonamide group selectivity. The utility of this approach in synthetic chemistry is demonstrated by the late-stage functionalization or synthesis of pharmaceutical molecules.