Selectfluor-mediated tandem cyclization of enaminones with diselenides toward the synthesis of 3-selenylated chromones
Ji-Hong Xia, Qian Chen, Jinwei Yuan, Weiqiong Shi, Liangru Yang, Yongmei Xiao
Abstract
A practical and metal-free approach for the regioselective selenation of chromones employing Selectfluor reagent under mild conditions is described. The developed method is suitable for a wide substrate scope and affords 3-selenylated chromones in good to excellent yield with high selectivity. An ionic mechanism is proposed for this transformation. Furthermore, the application of potassium thiocyanate with enaminones for the synthesis of thiocyano chromones in this transformation is also successful.
Topics & Concepts
SelectfluorChemistryRegioselectivityCombinatorial chemistryReagentPotassium thiocyanateTandemYield (engineering)Substrate (aquarium)SelectivityTransformation (genetics)TetrafluoroborateThiocyanateOrganic chemistryIonic liquidMaterials scienceCatalysisOceanographyBiochemistryComposite materialMetallurgyGeneGeologySulfur-Based Synthesis TechniquesOrganoselenium and organotellurium chemistrySynthesis of Organic Compounds