Electrochemically enabled nickel-catalyzed controllable synthesis of monoaryl or diaryl amines from aryl halides and trimethylsilyl azides†

Abstract

Aryl amines serve as fundamental building blocks in the production of many pharmaceuticals, agrochemicals, and functional materials, underscoring their preparation in synthetic chemistry. This work presents an approach that combines electrolysis with nickel catalysis to facilitate the C–N cross-coupling between aryl halides and trimethylsilyl azides (TMSN₃), marking a pioneering advancement in the direct synthesis of aryl amines from aryl halides via electrochemically enabled nickel catalysis. Furthermore, by adjusting the reaction conditions, this strategy could deliver monoaryl or diaryl amines chemoselectively. The approach exhibits broad substrate scope and robust functional group compatibility, allowing for the practical and versatile late-stage modification of complex pharmaceutical molecules.