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Issue 16, 2012
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Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones

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Abstract

α-Oxo gold carbenes generated via intermolecular oxidation of terminal alkynes are shown to be highly electrophilic and can effectively abstract halogen from halogenated solvents such as 1,2-dichloroethane or 1,2-dibromoethane. Chloro/bromomethyl ketones are prepared in moderate efficiencies in one step using Ph3PAuNTf2 as the catalyst and 8-methylquinoline N-oxide as the oxidant.

Graphical abstract: Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones

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Publication details

The article was received on 01 Feb 2012, accepted on 15 Feb 2012 and first published on 14 Mar 2012


Article type: Communication
DOI: 10.1039/C2OB25235J
Citation: Org. Biomol. Chem., 2012,10, 3168-3171
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    Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones

    W. He, L. Xie, Y. Xu, J. Xiang and L. Zhang, Org. Biomol. Chem., 2012, 10, 3168
    DOI: 10.1039/C2OB25235J

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