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, Email: rof2lehigh.edu

Y. Zhang, J. Jiao, R. A. Flowers, II, J. Org. Chem., 2006, 71, 4516-4520.

DOI: 10.1021/jo0602975 (free Supporting Information)

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Abstract

A mild, fast 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. The mechanism is discussed.

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proposed mechanism

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Key Words

Carboxylic Acids, Cerium Ammonium Nitrate

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ID: J42-Y2006-1490