有机化学 ›› 2012, Vol. 32 ›› Issue (04): 776-780.DOI: 10.6023/cjoc1109301 上一篇    下一篇

研究简报

缺电子芳香三氟甲磺酸酯与胺的氯化锌配合物的交叉偶联反应

徐娟, 史大昕, 魏真, 魏莹菲, 张奇, 李加荣   

  1. 北京理工大学化工与环境学院 北京 100081
  • 收稿日期:2011-09-30 修回日期:2011-11-22 出版日期:2012-04-25 发布日期:2012-04-24
  • 通讯作者: 李加荣 E-mail:jrli@bit.edu.cn

Ligand-Free Cross-Coupling of Electron-Poor Aryl Triflates with ZnCl2 Complexes of Amines

Xu Juan, Shi Daxin, Wei Zhen, Wei Yingfei, Zhang Qi, Li Jiarong   

  1. School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081
  • Received:2011-09-30 Revised:2011-11-22 Online:2012-04-25 Published:2012-04-24

采用新型的有机胺氯化锌配合物作为缺电子芳香三氟甲磺酸酯转化成芳胺的试剂, 研究发现反应可以在二甲基亚砜和碳酸钾的作用下进行, 无需隔氧、密封, 也不必加入配体. 提出了不同于经典SNAr 过程的机理, 并对生成的胺化产物进行了IR, MS 和1H NMR 表征.

关键词: 芳香C—N 键的构建, 芳胺, 缺电子芳香三氟甲磺酸酯, 胺的氯化锌配合物

The efficient conversion of electron-poor aryl triflates to the corresponding aromatic amines was accomplished by using ZnCl2 complexes of organic amines as nitrogen source with K2CO3 as the base in DMSO. The coupling reaction was performed in air and ligand-free without the sealed vessel. A possible mechanism, which was different with aromatic nucleophilic substitution (SNAr), was proposed. The amination products were confirmed by 1H NMR, IR and MS techniques.

Key words: formation of aromatic C—N bond, aromatic amine, electron-poor aryl triflates, ZnCl2 complexes of amines