Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 566-571.DOI: 10.6023/cjoc201308013 Previous Articles     Next Articles

Articles

金催化氧化末端炔烃合成α-乙酰氧基甲基酮方法研究

王小勇, 李治章   

  1. 湖南科技学院生命科学与化工系 永州 425100
  • 收稿日期:2013-08-11 修回日期:2013-11-04 发布日期:2013-11-14
  • 通讯作者: 李治章 E-mail:lzz5608@126.com
  • 基金资助:

    湖南省自然科学基金(No. 11JJ2009)和湖南省高校科技创新团队资助项目.

Gold(I)-Catalyzed Intermolecular Oxidation of Terminal Alkynes:Synthesis of α-Acetoxy Ketones

Wang Xiaoyong, Li Zhizhang   

  1. Department of Life Science and Chemical Engineering, Hunan University of Science and Engineering, Yongzhou 425100
  • Received:2013-08-11 Revised:2013-11-04 Published:2013-11-14
  • Supported by:

    Project supported by the Natural Science Foundation of Hunan Province (No. 11JJ2009) and the Sci-Tech Innovation Teams in Universities of Hunan Province.

In the presence of Ph3PAuNTf2, 8-methylquinoline-N-oxide and MsOH, various of terminal alkynes were efficiently converted into the corresponding α-acetoxy ketones. The influences of oxidant, catalyst structure, catalyst loading and reaction media on the reaction were investigated, and the optimal reaction conditions were also obtained. The reaction is proposed to proceed via α-oxo gold carbene intermolecular reaction with acetic acids. The reaction method with its advantages of simple procedure, mild reaction conditions and high yield provides a novel valuable approach to α-acetoxy ketones from terminal alkynes.

Key words: gold catalysis, alkynes, intermolecular oxidation, α-oxo gold carbene, α-acetoxy ketones