有机化学 ›› 2014, Vol. 34 ›› Issue (9): 1857-1863.DOI: 10.6023/cjoc201403062 上一篇    下一篇

研究论文

金催化炔烃与1,4-二氧六环的开环加成反应研究

鄢东, 吴超, 易卫国   

  1. 湖南化工职业技术学院, 株洲 412004
  • 收稿日期:2014-03-28 修回日期:2014-04-20 发布日期:2014-05-06
  • 通讯作者: 易卫国 E-mail:wgyi_hunan@126.com
  • 基金资助:

    湖南省科技厅基金(No. 2012FJ3039)和湖南省教育厅科学研究(No. 13C236)资助项目.

Gold-Catalyzed Alkynes Ring-Opening Addition Reaction with Dioxane

Yan Dong, Wu Chao, Yi Weiguo   

  1. Hunan Chemical Vocational Technology College, Zhuzhou 412004
  • Received:2014-03-28 Revised:2014-04-20 Published:2014-05-06
  • Supported by:

    Project supported by the Department of Science and Technology Foundation of Hunan Province (No. 2012FJ3039) and the Scientific Research Fund of Hunan Provincial Education Department (No. 13C236).

8-乙基喹啉氮氧化物为氧化剂,甲烷磺酸为添加酸,简单高效地实现了XphosAuCl/AgNTf2催化下末端炔烃与1,4-二氧六环的开环加成反应,以良好的收率获得了一系列带有不同取代基的甲磺酸羰基乙氧基乙酯化合物. 该反应原子经济性高、反应体系温和、底物适用范围广、产率良好.

关键词: 金催化剂, 炔烃, 开环反应, α-羰基金卡宾

A simple and efficient method for the ring-opening addition reaction of terminal alkyne with dioxane catalyzed by XphosAuCl/AgNTf2 was developed in presence of 8-ethylquinoline-N-oxide and methanesulfonic acid. A series of carbonylethoxy ethyl methanesulfonates were synthesized in good yield. The high atom economy, mild reaction system and a wide range of tolerated substrates make the reaction very practical.

Key words: gold catalyst, alkyne, ring-opening reaction, α-oxo gold carbene