PyfSeTs as a Novel and Photosensitive Reagent for the Green Light-Induced Arene C-H Selenenylation: A Verstile Strategy for the Synthesis of Aryl Selenides

Abstract

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