Abstract

The green and efficient synthesis of mono-, dis- and tri-substituted aryl sulfides and selenides was achieved via I2 mediated reaction of aromatic hydrocarbons with diphenyl disulfide or diselenide. A series of C–S and C–Se coupling products were obtained in good to excellent yield in the presence of 1.0 equiv. I2 using water as solvent at 90 °C. Our study showed that S–S and Se–Se bonds were activated by I2, which acted as a free radical initiator to generate PhS• and PhSe• free radicals, and conversion to C–S–C and C–Se–C bonds through a coupling reaction. The developed method achieves desirable products without using odorous and toxic thiols. This protocol is simple, highly efficiency, and avoids using metal catalyst, and acid and base additives.

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