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

doi:10.6023/cjoc201907046

摘要/Abstract

8-氨基喹啉的C（5）位碳-氢键氟化反应近年来受到广泛关注，但大多需要使用过渡金属催化剂和亲电氟化试剂来实现.在高价碘试剂的介导下实现了无过渡金属催化条件下的8-氨基喹啉C（5）位碳-氢键亲核氟化反应.使用廉价易得且安全稳定的氟化银作为亲核氟化试剂，反应无需惰性气体保护，条件简单，操作方便，区域选择性好，底物范围较广，为喹啉类化合物的氟化提供了一种有潜在应用价值的新方法.

关键词: 高价碘, 8-氨基喹啉, 亲核氟化, 氟化银

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

引用此文

陈倩雯, 杨耀成, 王霞, 张谦, 李栋. 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[J]. 有机化学, 2020, 40(2): 454-461.

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.

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