The copper-catalyzed mono- or dichalcogenation of aryl halide with sulfur or selenium can be carried out with the addition of aluminum. This method takes advantage of two properties of both the insertion of copper into the chalcogen-chalcogen bond and the reductive ability of aluminum. Furthermore, the addition of MgCl2 or Na2CO3 enables the selective synthesis of diaryl mono-chalcogenides or disulfides.
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Nobukazu Taniguchi (2005) studied this question.