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Issue 31, 2020
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MnO2 as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

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Abstract

Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(II) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.

Graphical abstract: MnO2 as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

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Supplementary files

Article information


Submitted
01 Jul 2020
Accepted
20 Jul 2020
First published
21 Jul 2020

Org. Biomol. Chem., 2020,18, 6115-6125
Article type
Paper

MnO2 as a terminal oxidant in Wacker oxidation of homoallyl alcohols and terminal olefins

R. A. Fernandes, G. V. Ramakrishna and V. Bethi, Org. Biomol. Chem., 2020, 18, 6115
DOI: 10.1039/D0OB01344G

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