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Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones

Bao‐Yin Zhao, Xinglong Zhang, Rui-Li Guo, Meng‐Yue Wang, Yaru Gao, Yong‐Qiang Wang

2021Organic Letters17 citationsDOI

Abstract

An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism has been investigated through deuterium-labeling experiments and intermediate experiments.

Topics & Concepts

DehydrogenationChemistryOxidative phosphorylationStereoselectivityFunctional groupCatalysisSubstrate (aquarium)Molecular oxygenCombinatorial chemistryAtom economyOrganic chemistryBiochemistryGeologyOceanographyPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsAsymmetric Hydrogenation and Catalysis