Copper-Catalyzed 8-Aminoquinoline Assisted Aryl Chalcogenation of Ferroceneamide with Aryl Disulfides, Diselenides, and Ditellurides

Abstract

A synthetic method has been developed for the synthesis of unsymmetrical ferrocene aryl chalcogenides by C-H activation of ferroceneamide using 8-aminoquinoline as a directing group, aryl dichalcogenides, and copper(II) catalyst in the presence of silver acetate oxidant at 80 °C in DMSO. The developed methodology is quite general and mild to access three unsymmetrical diaryl chalcogenides (sulfide, selenide, and telluride) and also amenable to aryl dichalcogenides with sensitive bromo, chloro, and nitro functionalities. Further, ferrocene aryl tellurides have been obtained in moderate yields for the first time by the developed C-H activation approach. In the mechanistic part, it seems that the presence of a rigid chelating directing ligand is crucial for the aryl chalcogenation reaction of C-H bond under copper catalysis as the nonrigid bidentate directing ligands were unsuccessful for the transformation.