4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl α-Halo Esters to Aryl α-Keto Esters

Jung, Yeonghun; Hong, Jee Eun; Baek, Seung Tae; Hong, Suckchang; Kwak, Jae-Hwan; Park, Yohan

doi:10.1021/acsomega.0c02511

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4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl α-Halo Esters to Aryl α-Keto Esters : 4-Dimethylaminopyridine-Catalyzed Metal-Free Aerobic Oxidation of Aryl alpha-Halo Esters to Aryl alpha-Keto Esters

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Authors: Jung, Yeonghun; Hong, Jee Eun; Baek, Seung Tae; Hong, Suckchang; Kwak, Jae-Hwan; Park, Yohan

Issue Date: 2020-09-15

Publisher: American Chemical Society

Citation: ACS Omega, Vol.5 No.36, pp.22951-22957

Abstract: A novel, metal-free aerobic oxidation method is described. 4-Dimethylaminopyridine (DMAP) successfully catalyzed the oxidation of aryl alpha-halo esters to corresponding aryl alpha-keto esters (up to 95% yield) under mild reaction conditions (Li2CO3, dimethylacetamide, air, and room temperature). A mechanism has been proposed where the oxidation proceeds through a [3 + 2] cycloaddition between O-2 in an air atmosphere and pyridinium ylides. The ylides are supposedly generated from aryl alpha-halo esters and DMAP in the presence of carbonates. Based on the plausible mechanism, the potential of DMAP as a catalyst in oxidation reactions was extended.