Synthesis 2013; 45(18): 2605-2611
DOI: 10.1055/s-0033-1338513
paper
© Georg Thieme Verlag Stuttgart · New York

Straightforward and Highly Efficient Synthesis of α-Acetoxy Ketones through Gold-Catalyzed Intermolecular Oxidation of Terminal Alkynes

Chao Wu
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821742   Email: wmhe@hnu.edu.cn   Email: jnxiang@hnu.edu.cn
,
Zhiwu Liang
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821742   Email: wmhe@hnu.edu.cn   Email: jnxiang@hnu.edu.cn
,
Dong Yan
b   Hunan Chemical Industry Vocation Technology Institute, Zhuzhou 412004, P. R. of China
,
Weimin He*
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821742   Email: wmhe@hnu.edu.cn   Email: jnxiang@hnu.edu.cn
,
Jiannan Xiang*
a   State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China   Fax: +86(731)88821742   Email: wmhe@hnu.edu.cn   Email: jnxiang@hnu.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 11.05.2013

Accepted after revision: 03.07.2013

Publication Date:
30 July 2013 (online)


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Abstract

A variety of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones through gold-catalyzed intermolecular oxidation in the presence of 8-methylquinoline 1-oxide as the oxidant. The reaction probably proceeds through an α-oxo gold carbene intermolecular O–H insertion.

Supporting Information