Atom Economical Photocatalytic Oxidation of Phenols and Site-Selective Epoxidation Toward Epoxyquinols
Louis Péault, Aurélien Planchat, Pierrick Nun, Erwan Le Grognec, Vincent Coeffard
Abstract
The discovery of a multiple-bond-forming process merging the singlet oxygen-mediated dearomatization of 3,4-disubstitued phenols and diastereo- and regioselective epoxidation is described. This one-pot strategy using a transition metal-free multicatalytic system comprised of rose bengal and cesium carbonate allowed the efficient formation of functionalized epoxyquinol products under mild conditions. Mechanistic investigations have been performed to shed the light on the key species involved in this transformation.
Topics & Concepts
RegioselectivitySinglet oxygenChemistryTransition metalPhenolsPhotocatalysisRose bengalCatalysisPhotochemistryCombinatorial chemistryCarbonateOrganic chemistryOxygenOxidative Organic Chemistry ReactionsOrganic Chemistry Cycloaddition ReactionsPolyoxometalates: Synthesis and Applications