有机化学 ›› 2015, Vol. 35 ›› Issue (3): 735-738.DOI: 10.6023/cjoc201408021 上一篇    下一篇

研究简报

1,7-二芳基-1,6-庚二炔化合物的合成

温燕梅, 谢建英, 冯润光, 黄绪明   

  1. 广东海洋大学理学院 湛江 524088
  • 收稿日期:2014-08-20 修回日期:2014-10-16 出版日期:2015-03-25 发布日期:2014-11-13
  • 通讯作者: 温燕梅 E-mail:wym1503@163.com
  • 基金资助:

    国家自然科学基金(No. 21172076)资助项目.

Synthesis of 1,7-Diarylhepta-1,6-diyne Compounds

Wen Yanmei, Xie Jianying, Feng Runguang, Huang Xuming   

  1. College of Science, Guangdong Ocean University, Zhanjiang 524088
  • Received:2014-08-20 Revised:2014-10-16 Online:2015-03-25 Published:2014-11-13
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21172076).

1,6-庚二炔是有机合成的重要中间体, 我们以PdCl2/CuI为催化剂, NEt3为碱, 在四氢呋喃溶剂中实现了二炔与卤代芳烃Sonogashira偶联反应, 合成了10个1,7-二芳基-1,6-庚二炔化合物, 该方法也适用于二卤芳烃如1,8-二碘萘与末端炔偶联合成1,8-二苯乙炔基萘. 所有合成的目标化合物结构经1H NMR, 13C NMR, IR 和MS表征.

关键词: 钯催化, 1,6-庚二炔, Sonogashira反应

Hepta-1,6-diynes are very useful synthetic intermediates. Using PdCl2/CuI as the catalyst and NEt3 as the base in tetrahedrofuran, ten 1,7-diarylhepta-1,6-diynes were synthesized by a simple Sonogashira coupling reaction of terminal diacetylenes and aryl halides. It is also indicated that 1,8-diiodonaphthalene can undergo the same transformation to 1,8- bis(phenylethynyl)naphthalene under typical conditions. Moreover, the structures of hepta-1,6-diyne derivatives were confirmed by 1H NMR, 13C NMR, IR and MS techniques.

Key words: Palladium-catalyzed, Hepta-1,6-diyne, Sonogashira reaction