Hu Meiqian, Zhang Shuai, Qin Changsheng, Nie Hongsheng, Xiong Zhicheng, Shi Xiaoyu, Zhao Yumiao, Li Mingzhe, Wang Shoucai, Ji Fanghua, Jiang Guangbin
Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, People's Republic of China.
J Org Chem. 2023 Sep 15;88(18):12958-12970. doi: 10.1021/acs.joc.3c00876. Epub 2023 Aug 24.
This work describes an effective C3-H halogenation of quinoline-4(1)-ones under electrochemical conditions, in which potassium halides serve as both halogenating agents and electrolytes. The protocol provides expedient access to different halogenated quinoline-4(1)-ones with unique regioselectivity, broad substrate scope, and gram-scale synthesis employing convenient, environmentally friendly electrolysis, in an undivided cell. Mechanism studies have shown that halogen radicals can promote the activation of N-H bonds in quinolones.
这项工作描述了喹啉-4(1)-酮在电化学条件下有效的C3-H卤化反应，其中卤化钾既作为卤化剂又作为电解质。该方法通过简便、环境友好的电解方式，在无隔膜电解池中，以独特的区域选择性、广泛的底物范围和克级规模合成，方便地获得不同的卤代喹啉-4(1)-酮。机理研究表明，卤素自由基可促进喹啉酮中N-H键的活化。
