Mild Conversion of β-Diketones and β-Ketoesters to Carboxylic Acids

Yang Zhang, Jingliang Jiao, and Robert A. Flowers, II*
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015
J. Org. Chem., 2006, 71 (12), pp 4516–4520
DOI: 10.1021/jo0602975
Publication Date (Web): May 13, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, rof2@lehigh.edu

Abstract

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A mild protocol for the conversion of β-ketoesters and β-diketones to carboxylic acids with use of CAN in CH3CN is described. The method is compatible with a number of functional groups, and can generate carboxylic acids under neutral conditions at room temperature. The reaction is fast and general, providing an alternative method to the commonly used malonic ester acid preparation. Initial mechanistic studies show that initial oxidation of the enol form of the β-dicarbonyl initiates the reaction. The presence of nitrate as an oxidant ligand or as an additive is critical for success of the reaction.

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History

  • Published In Issue June 09, 2006
  • Received February 13, 2006

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