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Issue 3, 2010
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Oxygen-assisted cross-coupling of methanol with alkyl alcohols on metallic gold

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Abstract

We demonstrate for the first time that selective cross-coupling of methanol with either ethanol or n-butanol occurs below room temperature on metallic gold with no metal oxide support in a reaction sequence that occurs entirely on the surface. The esterification proceeds via activation of the alcohols by adsorbed oxygen and a sequence of reactions that involve both surface-bound alkoxys and hemiacetals as intermediates. The reaction selectivity is dictated by competing β-hydride elimination from the alkoxys. Due to the higher activation energy for β-hydride elimination from methoxy, no formate esters are formed. A molecular-scale mechanism constructed using our results is in excellent agreement with studies of heterogeneous catalysts, providing insight into selectivity control under a broad range of conditions.

Graphical abstract: Oxygen-assisted cross-coupling of methanol with alkyl alcohols on metallic gold

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Article information


Submitted
05 Mar 2010
Accepted
14 May 2010
First published
24 Jun 2010

Chem. Sci., 2010,1, 310-314
Article type
Edge Article

Oxygen-assisted cross-coupling of methanol with alkyl alcohols on metallic gold

B. Xu, J. Haubrich, C. G. Freyschlag, R. J. Madix and C. M. Friend, Chem. Sci., 2010, 1, 310
DOI: 10.1039/C0SC00214C

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