4.8 Article

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

Journal

ORGANIC LETTERS
Volume 13, Issue 16, Pages 4164-4167

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2014335

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Funding

  1. Studienstiftung des deutschen Volkes

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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 center dot 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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