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. 2011 Aug 19;13(16):4164-7.
doi: 10.1021/ol2014335. Epub 2011 Jul 27.

TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates

Andrea-Katharina C Schmidt  1 , Christian B W Stark
Affiliations

TPAP-catalyzed direct oxidation of primary alcohols to carboxylic acids through stabilized aldehyde hydrates

Andrea-Katharina C Schmidt et al. Org Lett. .

Abstract

We present a simple, mild, and highly effective method for the direct conversion of primary alcohols to carboxylic acids. TPAP serves as the catalyst, and NMO·H(2)O 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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