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

Chao Wu, Zhiwu Liang, Dong Yan, Weimin He*, Jiannan Xiang*

*State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China, Email: wmhehnu.edu.cn, jnxianghnu.edu.cn

C. Wu, Z. Liang, D. Yan, W. He, J. Xiang, Synthesis, 2013, 45, 2605-2611.

DOI: 10.1055/s-0033-1338513 (free Supporting Information)


Abstract

Gold-catalyzed intermolecular oxidation enables an efficient conversion of various terminal alkynes into the corresponding α-acetoxy ketones 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.

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Key Words

alkynes, homogeneous catalysis, gold, oxidations, carbene complexes, ketones, esters, hydration, hydroxy ketones, N-oxides


ID: J66-Y2013