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Issue 39, 2014
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Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids

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Abstract

An oxidation of allylic and benzylic alcohols to the corresponding carboxylic acids is effected by merging a Cu-catalyzed oxidation using O2 as a terminal oxidant with a subsequent chlorite oxidation (Lindgren oxidation). The protocol was optimized to obtain pure products without chromatography or crystallization. Interception at the aldehyde stage allowed for Z/E-isomerization, thus rendering the oxidation stereoconvergent with respect to the configuration of the starting material.

Graphical abstract: Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids

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Publication details

The article was received on 19 Feb 2014, accepted on 21 Mar 2014 and first published on 26 Mar 2014


Article type: Communication
DOI: 10.1039/C4CC01305K
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Chem. Commun., 2014,50, 5014-5016
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    Oxidation of allylic and benzylic alcohols to aldehydes and carboxylic acids

    D. Könning, T. Olbrisch, F. D. Sypaseuth, C. C. Tzschucke and M. Christmann, Chem. Commun., 2014, 50, 5014
    DOI: 10.1039/C4CC01305K

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