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. This method utilizes readily available substrates to provide the desired products in moderate to good yields. Moreover, the practicality of the reaction is demonstrated through its successful application on a gram scale. 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.