Regio- and Stereoselective Synthesis of 3-Selenylazaflavanones and 3-Selenylflavanones via Electrochemically Facilitated Selenylation Cascade
Shaogao Zeng, Yong Zeng, Hui Wang, Pinghua Sun, Zhixiong Ruan
Abstract
Herein, an oxidant- and metal-free electrochemical selenylation reaction of chalcones with diselenides for the synthesis of 3-selenylazaflavanones and 3-selenylflavanones at room temperature was reported. The method proceeded under mild conditions, exhibited a broad substrate scope, and provided the selenylated products in moderate to excellent yields with high regio- and stereoselectivity. The reaction could also be readily scaled up with high efficiency. Detailed mechanistic studies through control experiments disclosed that a selenium-based radical might participate in this electrochemical transformation.
Topics & Concepts
ChemistryStereoselectivitySubstrate (aquarium)ElectrochemistryCascadeCombinatorial chemistrySeleniumRegioselectivityOrganic chemistryPhysical chemistryCatalysisChromatographyElectrodeOceanographyGeologySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryRadical Photochemical Reactions