Transition-Metal-catalyzed Synthesis of Organomonochalcogenide Compounds by Cleavage of the Dichalcogenide Bond

A transition metal-catalyzed aryl carbon-chalcogen bond formation has been well performed by a combination of aryl halides and thiol or selenol under basic conditions. However, a catalytic process using dichalcogenides has been rarely explored to date. We have developed copper or nickel-catalyzed procedures, which realize preparation of unsymmetrical mono-chalcogenides from dichalcogenides with aryl halides under reductive conditions or with organoboronic acids under oxidative conditions. Furthermore, these reactions can utilize both organochalcogenide-groups on dichalcogenide.