有机化学 ›› 2017, Vol. 37 ›› Issue (10): 2678-2684.DOI: 10.6023/cjoc201704049 上一篇    下一篇

研究论文

镍催化的8-氨基喹啉C—H键卤化反应合成C(5)和C(7)双卤代喹啉

郝文燕, 王昱赟, 杨国敏, 刘云云   

  1. 江西师范大学化学化工学院 南昌 330022
  • 收稿日期:2017-04-28 修回日期:2017-06-23 发布日期:2017-07-04
  • 通讯作者: 郝文燕, 刘云云 E-mail:wenyanhao@jxnu.edu.cn;chemliuyunyun@jxnu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21562024,21762023)及江西省教育厅(No.GJJ160285)资助项目.

Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines

Hao Wenyan, Wang Yuyun, Yang Guomin, Liu Yunyun   

  1. College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022
  • Received:2017-04-28 Revised:2017-06-23 Published:2017-07-04
  • Contact: 10.6023/cjoc201704049 E-mail:wenyanhao@jxnu.edu.cn;chemliuyunyun@jxnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos.21562024,21762023) and the Scientific Research Fund of Jiangxi Provincial Education Department (No.GJJ160285).

以廉价、低毒、易得的溴化镍做催化剂,实现了8-氨基喹啉环上的氧化C-H键卤化反应.该方法利用氧气作为氧化剂,避免使用化学当量的高价碘盐等作为氧化剂,使得本反应更具经济性和环境友好性.在该催化体系下反应底物显示出良好的官能团兼容性和反应性,并以高的区域选择性高产率地制备了C(5)和C(7)双卤代喹啉.

关键词: 镍催化, C—H键卤化, N-溴代丁二酰亚胺, 8-氨基喹啉, 双卤代喹啉

A simple and efficient nickel-catalyzed oxidative halogenation (Cl, Br) of C(5) and C(7) C-H bond of 8-aminoquinoline amides has been developed. This method employed low-cost and easy availability nickel as catalyst and oxygen as oxidant. The reactions have good functional groups compatibility, giving highly selective C(5) and C(7) di-halogenated products in good to excellent yields.

Key words: Nickel-catalyze, C—H halogenation, N-bromo-succinimide, 8-aminoquinolines, dihalogenated quinoline