PyfSeTs as a novel and photosensitive reagent for green light-induced arene C–H selenenylation: a versatile strategy for the synthesis of aryl selenides

Abstract

Herein, we report the discovery of a novel and photosensitive seleno donor reagent, Se-(perfluoropyridin-4-yl) 4-methylbenzenesulfonoselenoate (PyfSeTs), for green light-induced site selective C–H selenation of a variety of arenes using molecular oxygen as the oxidant. In particular, the perfluoropyridylselenyl group of the product could be activated using a redox process, enabling the generation of active selenium species for various transformations and offering a versatile platform for C–Se bond construction and arylselenide synthesis. The preparative power of the transformations has been further highlighted in the synthesis of selenoflavones and their analogues, which leads to the discovery of two attractive lead compounds for anticancer drug discovery.