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Issue 43, 2015
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Titanium superoxide – a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant

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Abstract

Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this “one pot” direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide–aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.

Graphical abstract: Titanium superoxide – a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant

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Publication details

The article was received on 30 Jul 2015, accepted on 27 Aug 2015 and first published on 04 Sep 2015


Article type: Paper
DOI: 10.1039/C5OB01586C
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Citation: Org. Biomol. Chem., 2015,13, 10631-10640

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    Titanium superoxide – a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant

    S. Dey, S. K. Gadakh and A. Sudalai, Org. Biomol. Chem., 2015, 13, 10631
    DOI: 10.1039/C5OB01586C

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