This work describes the facile synthesis of 5-arylselenyluracils via bromide-catalyzed three-component reaction of Se powder, boronic acids, and uracils under metal-free and strong-oxidant-free conditions. Simple catalytic conditions, high efficiency, good functional group compatibility, easily applicable for gram-scale reaction, and a radical pathway are shown in this method.

Abstract

Herein, an efficient method for the synthesis of 5-arylselenyluracils via bromide-catalyzed selective C(sp² )-H selenylation of uracils using boronic acid and elemental selenium as the selenyl source was successfully developed. This method proceeded smoothly for a series of arylboronic acids and uracils under metal-free and strong oxidant-free conditions. This protocol offered simple catalytic conditions, high efficiency, good functional group compatibility, easy operation, and easy scalable. Furthermore, the mechanistic studies suggested that this transformation was possibly undergone via a radical pathway.