有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1237-1245.DOI: 10.6023/cjoc201701034 上一篇    下一篇

研究论文

钴催化的8-氨基喹啉C(5)位的苄基化反应

张家恒, 郝新奇, 王正龙, 任常久, 牛俊龙, 宋毛平   

  1. 郑州大学化学与分子工程学院 郑州 450000
  • 收稿日期:2017-01-16 修回日期:2017-02-22 发布日期:2017-03-03
  • 通讯作者: 牛俊龙,宋毛平 E-mail:niujunlong@zzu.edu.cn;mpsong@zzu.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21502173,21272217)、郑州大学优秀青年人才研究基金(No.1521316002)资助项目.

Cobalt-Catalyzed C-H Benzylation of 8-Aminoquinolines on C(5) Position

Zhang Jiaheng, Hao Xinqi, Wang Zhenglong, Ren Changjiu, Niu Junlong, Song Maoping   

  1. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450000
  • Received:2017-01-16 Revised:2017-02-22 Published:2017-03-03
  • Contact: 10.6023/cjoc201701034 E-mail:niujunlong@zzu.edu.cn;mpsong@zzu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21502173, 21272217), the Outstanding Young Talent Research Fund of Zhengzhou University (No. 1521316002).

研究了首例钴催化下氨基喹啉C(5)位的苄基化反应.在120℃条件下,以四水合醋酸钴为催化剂,三氟乙酸银为氧化剂,溴苯为溶剂,8-氨基喹啉酰胺与2,6-二叔丁基-4-甲基苯酚(BHT)通过C(sp2)-H与C(sp3)-H的交叉偶联高产率得到了目标产物.该反应具有较好的底物普适性,为8-氨基喹啉C(5)位苄基类化合物的合成提供了一种有效方法.

关键词: 8-氨基喹啉, 苄基化, 钴, 交叉偶联

The first cobalt-catalyzed benzylation of aminoquinolines on C(5) position has been developed. The C(sp2)-H/ C(sp3)-H cross-coupling of quinolineamides and butylated hydroxytoluene (BHT) could yield the desired products via bidentate-chelation assistance. Under the optimal reaction condition of Co(OAc)2·4H2O (20 mol%), AgTFA (2.0 equiv.), 120 ℃ for 12 h, the reaction is compatible with a wide range of quinoline substrates. This protocol provides a facile access to the benzyl substituted quinolines.

Key words: 8-aminoquinoline, benzylation, cobalt, cross-coupling