Oxidation of alcohols to aldehydes or ketones using stoichiometric 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1  ) in CH2Cl2 at room temperature is a highly selective process favoring reaction at the carbinol center best able to accommodate a positive charge. The oxidation of alcohols to carboxylic acids by 1 in wet acetonitrile is also selective; the rate of the process correlates with the concentration of aldehyde hydrate intermediate. As illustrated below, a convenient method for oxidation of alcohols to carboxylic acids has been developed.

Oxoammonium salt oxidation of alcohols to aldehydes and carboxylic acids

245th National Meeting (2013)

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