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Issue 9, 2013
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Alkyl groups as synthetic vehicles in gold-mediated oxidative coupling reactions

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Abstract

The use of surface-bound alkyl and phenyl groups as synthetic vehicles in coupling reactions on oxygen-activated Au(111) is demonstrated by the formation of ethers via alkyl and phenyl iodides. Ethers are formed by successive additions of surface-bound alkyl groups to adsorbed atomic oxygen to form first the alkoxy and then the ether. The addition of the ethyl group to adsorbed oxygen on Au(111) is the rate-limiting step leading to diethyl ether formation. Alkyl groups also add to adsorbed alkoxy groups formed from alcohols. An unusual feature of the alkyl iodide reactions on Au is that oxygen is not required for the activation step; hence, opening new potential reactive pathways on metallic Au.

Graphical abstract: Alkyl groups as synthetic vehicles in gold-mediated oxidative coupling reactions

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Article information


Submitted
06 Nov 2012
Accepted
11 Jan 2013
First published
11 Jan 2013

Phys. Chem. Chem. Phys., 2013,15, 3179-3185
Article type
Paper

Alkyl groups as synthetic vehicles in gold-mediated oxidative coupling reactions

B. Xu, R. J. Madix and C. M. Friend, Phys. Chem. Chem. Phys., 2013, 15, 3179
DOI: 10.1039/C3CP43956A

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