TPAP-Catalyzed Direct Oxidation of Primary Alcohols to Carboxylic Acids through Stabilized Aldehyde Hydrates

Andrea-Katharina C. Schmidt and Christian B. W. Stark*

*Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany, Email: starkchemie.uni-hamburg.de

A.-K. C. Schmidt, C. B. W. Stark, Org. Lett., 2011, 13, 4164-4167.

DOI: 10.1021/ol2014335

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Abstract

In a simple, mild, and highly effective method for the direct conversion of primary alcohols to carboxylic acids, TPAP serves as the catalyst, and NMO • H₂O plays a dual role, acting as the co-oxidant and as a reagent for aldehyde hydrate stabilization. This previously unknown stabilizing effect of geminal diols by N-oxides is the key for the efficiency of the overall transformation.

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Key Words

Carboxylic Acids, TPAP, NMO

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ID: J54-Y2011-2240