Photoredox-Mediated Aerobic Oxidative Cleavage of 1,3-Diketones to Access 1,2-Diketones and (<i>Z</i>)-1,4-Enediones
Xiaofeng Yu, Nan Huang, Yanping Huo, Xianwei Li, Yan Liu, Keiji Maruoka, Qian Chen
Abstract
An aerobic oxidative cleavage of 1,3-diketones under visible light irradiation using an organic dye as a photocatalyst is disclosed. The newly developed reaction provides practical access to 1,2-diketones and ( Z )-1,4-enediones in moderate to good yields with absolute regio- and stereoselectivity. Mechanistic studies of the reaction suggest that tetraketone intermediates might undergo a photocatalytic energy transfer from the excited photocatalyst to form biradical-like (n,π*) states of ketones.
Topics & Concepts
ChemistryOxidative cleavagePhotocatalysisOxidative phosphorylationStereoselectivityPhotochemistryCleavage (geology)Excited stateDiketoneMedicinal chemistryIrradiationPhotoredox catalysisKetoneCatalysisOrganic chemistryBiochemistryEngineeringPhysicsNuclear physicsGeotechnical engineeringFracture (geology)Radical Photochemical ReactionsOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization Methods