有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2199-2204.DOI: 10.6023/cjoc201505033 上一篇    下一篇

研究简报

钯催化炔酸与烯烃串联碳酯化反应研究

李建晓a, 张振明a, 李春生a, 罗维b, 杨少容a   

  1. a 华南理工大学化学与化工学院 广州 510640;
    b 华南理工大学分析测试中心 广州 510640
  • 收稿日期:2015-05-21 修回日期:2015-06-05 出版日期:2015-10-25 发布日期:2015-06-16
  • 通讯作者: 杨少容 E-mail:lisryang@scut.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21102047, 31101221)和中国博士后科学基金(No. 2015M572303)资助项目.

Palladium-Catalyzed Intermolecular Carboesterification of Alkynoic Acids with Alkenes

Li Jianxiaoa, Zhang Zhenminga, Li Chunshenga, Luo Weib, Yang Shaoronga   

  1. a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
    b Analytical and Testing Center, South China University of Technology, Guangzhou 510640
  • Received:2015-05-21 Revised:2015-06-05 Online:2015-10-25 Published:2015-06-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221) and the China Postdoctoral Science Foundation (No. 2015M572303).

室温条件下, 以离子液体为溶剂, 利用炔酸与烯烃衍生物发生串联碳酯化反应, 以中等至优良产率(58%~83%)合成系列官能团化的α-亚甲基-γ-丁内酯衍生物. 其结构均经IR, 1H NMR, 13C NMR及HRMS确证. 该串联反应具有反应条件温和、底物适用范围广、环境友好等优点, 可为具有α-亚甲基-γ-丁内酯骨架的天然产物及复杂药物分子的合成提供简便的途径.

关键词: 钯催化, 离子液体, 炔酸, 烯烃, 碳酯化反应

An efficient and mild palladium-catalyzed cascade carboesterification has been developed to afford functionalized α-methylene-γ-lactones in moderate to good yields with high regio-and diastereo-selectivities. Their structures were confirmed by IR, 1H NMR, 13C NMR and HRMS. Furthermore, this reaction provided a novel and convenient methodology for the construction of naturally occurring biologically active α-methylene-γ-lactones.

Key words: palladium-catalyzed, ionic liquids, alkynoic acids, alkenes, carboesterification