Regioselective <i>peri</i>-C–H selenylation of aromatic compounds with weakly coordinating ketone groups
Bingbing Duan, Yao Wu, Yi Gao, Linkun Ying, Jielin Tang, Shiyu Hu, Qiuhua Zhao, Zengqiang Song
Abstract
-C-H selenylation of aromatic compounds bearing ketone groups, including chromones, xanthones, acridinones, quinolinones and naphthoquinones with diselenides under Ru(II) catalysis is presented. Various chromones and diselenides are applicable for this transformation, affording 5-selenyl chromones in a highly regioselective manner in good to excellent yields. This transformation is easy to scale up and the desired products can be further modified. Most importantly, this transformation allows the late-stage selenylation of bioactive compounds. Mechanistic studies show that radicals may be involved in this novel transformation.
Topics & Concepts
RegioselectivityKetoneChemistryTransformation (genetics)CatalysisCombinatorial chemistryOrganic chemistryGeneBiochemistrySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistryCatalytic C–H Functionalization Methods