Copper(II) Acetate-Catalyzed Aerobic Oxidation of N -(2-Arylacetyl)-1,3-oxazolidin-2-ones to 1,2-Dicarbonyl Compounds

The copper-catalyzed aerobic oxidation of N-(2-arylacetyl)-1,3-oxazolidin-2-ones to the corresponding 2-oxo derivatives is described. The transformation is promoted by copper(II) acetate and 1,10-phenanthroline in DMSO at 30 °C and provides a wide range of 1,2-dicarbonyl compounds under mild reaction conditions. The method does not require bases or additional reagents, avoids prolonged heating, and proceeds through an operationally simple process with minimal waste generation. Eventually, the resulting α-keto imides can be readily converted into α-keto esters or amides and α-hydroxy derivatives.

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Journal
The Journal of Organic Chemistry
Published
2026-10-13
DOI
https://doi.org/10.1021/acs.joc.6c01792
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
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article

Copper(II) Acetate-Catalyzed Aerobic Oxidation of N -(2-Arylacetyl)-1,3-oxazolidin-2-ones to 1,2-Dicarbonyl Compounds

Pedro Romea, Anna Maria Costa, Eduard Balaguer-Garcia, Fèlix Urpı́ et al.
The Journal of Organic Chemistry
Oxidative Organic Chemistry Reactions
article

Copper(II) Acetate-Catalyzed Aerobic Oxidation of N -(2-Arylacetyl)-1,3-oxazolidin-2-ones to 1,2-Dicarbonyl Compounds

Pedro Romea, Anna Maria Costa, Eduard Balaguer-Garcia, Fèlix Urpı́, Pol Castillo-Torres, Tanja Sundman
article en

Abstract

The copper-catalyzed aerobic oxidation of N-(2-arylacetyl)-1,3-oxazolidin-2-ones to the corresponding 2-oxo derivatives is described. The transformation is promoted by copper(II) acetate and 1,10-phenanthroline in DMSO at 30 °C and provides a wide range of 1,2-dicarbonyl compounds under mild reaction conditions. The method does not require bases or additional reagents, avoids prolonged heating, and proceeds through an operationally simple process with minimal waste generation. Eventually, the resulting α-keto imides can be readily converted into α-keto esters or amides and α-hydroxy derivatives.

The Journal of Organic Chemistry
Universitat de Barcelona (ES)
Ministerio de Ciencia, Innovación y Universidades, Generalitat de Catalunya, Agencia Estatal de Investigación
Openalex Percentile: Top 25%
Oxidative Organic Chemistry Reactions
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