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, L Zhang

Index: He, Weimin; Xie, Longyong; Xu, Yingying; Xiang, Jiannan; Zhang, Liming Organic and Biomolecular Chemistry, 2012 , vol. 10, # 16 p. 3168 - 3171

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Citation Number: 58

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.