Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 454-461.DOI: 10.6023/cjoc201907046 Previous Articles     Next Articles

Special Issue: 有机氟化学合辑

高价碘试剂介导的8-氨基喹啉C(5)位碳-氢键亲核氟化反应

陈倩雯, 杨耀成, 王霞, 张谦, 李栋   

  1. 湖北工业大学材料与化学工程学院 武汉 430068
  • 收稿日期:2019-07-28 修回日期:2019-09-19 发布日期:2019-10-12
  • 通讯作者: 李栋 E-mail:dongli@mail.hbut.edu.cn
  • 基金资助:
    国家自然科学基金(No.21702054)和大学生创新创业训练计划(No.201610500005)资助项目.

Hypervalent Iodine Reagent-Mediated C(5) C-H Nucleophilic Fluorination of 8-Aminoqunolines

Chen Qianwen, Yang Yaocheng, Wang Xia, Zhang Qian, Li Dong   

  1. College of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068
  • Received:2019-07-28 Revised:2019-09-19 Published:2019-10-12
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21702054) and the Innovation and Entrepreneurship Training Program (No. 201610500005).

The C(5) C-H fluorination of 8-aminoqunolines has attracted much attention recently. However, transition-metal catalyst and electrophilic fluorination reagents were required in most of these reactions. Transition-metal catalyst free C(5) C-H nucleophilic fluorination of 8-aminoqunolines was reviewed. This reaction was mediated by a hypervalent iodine reagent and employed cheap, safe and stable silver fluoride as the nucleophilic fluorination reagent. The reaction proceeded without inert gas protection. It possess the merits of simple and mild reaction conditions, easy operation, high regioselectivity and wide substrate scope and provides a novel method for fluorination of quinolines with potential application value.

Key words: hypervalent iodine, 8-aminoqunoline, nucleophilic fluorination, silver fluoride