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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 2: 454 - 461

DOI: https://doi.org/10.6023/cjoc201907046

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

  • Chen Qianwen ,
  • Yang Yaocheng ,
  • Wang Xia ,
  • Zhang Qian ,
  • Li Dong
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  • College of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068

Received date: 2019-07-28

  Revised date: 2019-09-19

  Online 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).

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Abstract

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

Cite this article

Chen Qianwen , Yang Yaocheng , Wang Xia , Zhang Qian , Li Dong . Hypervalent Iodine Reagent-Mediated C(5) C-H Nucleophilic Fluorination of 8-Aminoqunolines[J]. Chinese Journal of Organic Chemistry, 2020 , 40(2) : 454 -461 . DOI: 10.6023/cjoc201907046

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