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

Yeonghun Jung | Zendy; Jee Eun Hong | Zendy; Seung Tae Baek | Zendy; Suckchang Hong | Zendy; JaeHwan Kwak | Zendy; Yohan Park | Zendy

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

Author(s) -

Yeonghun Jung,

Jee Eun Hong,

Seung Tae Baek,

Suckchang Hong,

JaeHwan Kwak,

Yohan Park

Publication year - 2020

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.0c02511

Subject(s) - aryl , chemistry , catalysis , pyridinium , dimethylacetamide , metal , organic chemistry , medicinal chemistry , yield (engineering) , cycloaddition , alkyl , materials science , solvent , metallurgy

A novel, metal-free aerobic oxidation method is described. 4-Dimethylaminopyridine (DMAP) successfully catalyzed the oxidation of aryl α-halo esters to corresponding aryl α-keto esters (up to 95% yield) under mild reaction conditions (Li 2 CO 3 , 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 α-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.

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