Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


see article for more reactions

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.

see article for more examples



Key Words

Carboxylic Acids, TPAP, NMO


ID: J54-Y2011-2240