Issue 16, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Weimin He,a   Longyong Xie,a   Yingying Xu,a   Jiannan Xiang*a  and  Liming Zhang*b  

* Corresponding authors

a College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha, P.R. of China
E-mail: jnxiang@hnu.edu.cn

b Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106, United States
E-mail: zhang@chem.ucsb.edu
Fax: +1 (805)893-4120
Tel: +1 (805)893-7392

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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Article information

DOI
https://doi.org/10.1039/C2OB25235J
Article type
Communication
Submitted
01 Feb 2012
Accepted
15 Feb 2012
First published
14 Mar 2012

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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