Copper-catalyzed N-H bond chalcogenation of anilines

The chalcogen-nitrogen bond (X-N, where X = S, Se) is a key chemical motif in many structures, including inorganic and organic materials, catalysts, protein mimics, and pharmaceuticals. Consequently, developing mild and general methods for constructing N-S and N-Se bonds is important in organic synthesis. Herein, we have developed a novel copper-catalyzed approach to form N-S/N-Se bonds by coupling amines with 1,2-diphenyl disulfide or diphenyl diselenide. The disclosed platforms demonstrate excellent substrate scope, delivering the desired products in good to excellent yields, and are readily amenable for scale-up. The configuration of the product was confirmed through single-crystal X-ray diffraction analysis. Hitherto, no prior reports have been found in the literature for forming N-Se bonds making this reaction an important breakthrough in synthetic organic chemistry.