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: wmhe
hnu.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
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
