有机化学 ›› 2014, Vol. 34 ›› Issue (6): 1148-1153.DOI: 10.6023/cjoc201401017 上一篇    下一篇

研究论文

离子液体中钯催化合成cis-1, 2-二卤代-1, 7-辛二烯的反应研究

杨少容a, 凌厂围a, 马建业a, 张蕾a, 李建晓a, 罗维b   

  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:2014-01-10 修回日期:2014-02-24 出版日期:2014-06-25 发布日期:2014-03-03
  • 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)和华南理工大学学生研究计划资助项目.

Synthesis of cis-1, 2-Dihalosubstituted 1, 7-Octadienes by Pd-Catalyzed Cross-Coupling Reaction in Ionic Liquids

Yang Shaoronga, Ling Changweia, Ma Jianyea, Zhang Leia, Li Jianxiaoa, Luo Weib   

  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:2014-01-10 Revised:2014-02-24 Online:2014-06-25 Published:2014-03-03
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221) and the South China University of Technology Student Research Project.

发展了一种以PdBr2为催化剂,以[Bmim]X/HXaq为溶剂,炔卤与5-己烯-1-醇进行交叉偶联反应的新方法,以中等及优良的产率(73%~94%)合成了系列cis-1,2-二卤代-1,7-辛二烯衍生物. 反应表现出较高的区域选择性和立体选择性. 并且该偶联反应合成途径简捷、反应条件温和,可为cis-1,2-二卤代烯烃类化合物的合成提供简便的途径.

关键词: 离子液体, 钯催化, 炔卤, 5-己烯-1-醇, cis-1,2-二卤代烯烃

A Pd-catalyzed method was developed for cross-coupling reaction of a wide range of haloalkynes with hex-5-en-1-ol in ionic liquids. In the presence of PdBr2, [Bmim]X and HXaq, the cross-coupling products can be obtained in moderate to good yields, and the reaction displayed high regio- and stereo-selectivities. Moreover, the reaction is a convenient and simple path for the synthesis of the cis-1,2-dihalosubstituted alkenes, and tolerates several functional groups on haloalkynes.

Key words: ionic liquids, palladium-catalyst, haloalkynes, hex-5-en-1-ol, cis-1,2-dihalosubstituted alkenes