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

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

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...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-04, Vol.10 (16), p.3168-3171
Hauptverfasser: He, Weimin, Xie, Longyong, Xu, Yingying, Xiang, Jiannan, Zhang, Liming
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container_issue 16
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container_title Organic & biomolecular chemistry
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creator He, Weimin
Xie, Longyong
Xu, Yingying
Xiang, Jiannan
Zhang, Liming
description 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 Ph(3)PAuNTf(2) as the catalyst and 8-methylquinoline N-oxide as the oxidant.
doi_str_mv 10.1039/c2ob25235j
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title Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones
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