Chalcogenylation of 4-Hydroxycoumarins and 4-Hydroxyquinolinones in Water at Room Temperature

Abstract

A mild and efficient method has been developed for the synthesis of 3-selenyl and 3-sulfenyl derivatives of 4-hydroxycoumarins and 4-hydroxyquinolinones via an iodine-promoted reaction in aqueous media at room temperature. This approach involves the direct coupling of 4-hydroxycoumarins with diphenyl diselenides or thiols and demonstrates good functional group tolerance, affording the desired products in moderate to high yields. A series of control experiments were conducted to propose plausible reaction pathways, providing a foundation for further research into sulfur and selenium functionalization. The practicality of this method was further demonstrated by its successful application in the synthesis of 3,3’-sulfenyl-bis-4-hydroxycoumarins.