Radical C-H Selenylation of 8-Aminoquinolines with Se Powder and Boronic Acids via Bromide Catalysis

Herein, we report a robust and metal-free platform that allows the facile synthesis of 5-organoselenylated 8-aminoquinolines via bromide-catalyzed remote C-H radical coupling under metal-free and strong oxidant-free conditions. This protocol enabled the formation of a C-Se bond with high efficiency under the synergistic work of ammonium bromide, dimethyl sulfoxide, and air, offering a series of 5-organoselenyl-8-aminoquinolines in moderate to good yields. The present protocol was highlighted by its simple catalytic system, low cost, commercially available selenyl source, operational simplicity, broad substrate scope, accommodating across extensive functional group tolerance, gram-scale synthesis, and valuable postfunctionalizations. Furthermore, a radical pathway was possibly integrated in this transformation, which was supported by the detailed mechanistic studies.