有机化学 ›› 2022, Vol. 42 ›› Issue (2): 641-649.DOI: 10.6023/cjoc202108023 上一篇    下一篇

所属专题: 有机氟化学虚拟合辑

研究论文

电化学氧化下喹喔啉-2(1H)-酮的三氟甲基化及电描述符对反应性能的评价

锅小龙a, 王玉贤a, 赵志强a, 王庆a, 左剑b,*(), 王陆瑶a,*()   

  1. a 首都师范大学化学系 北京 100048
    b 首都师范大学物理系 北京 100048
  • 收稿日期:2021-08-16 修回日期:2021-09-19 发布日期:2022-02-24
  • 通讯作者: 左剑, 王陆瑶
  • 基金资助:
    国家自然科学基金(22074095); “十三五”期间北京市属高校高水平教师(CIT&TCD20190330)

Electrochemical Oxidative C—H Trifluoromethylation of Quinoxalin-2(1H)-ones and the Performance Evaluation via Electro-descriptors

Xiaolong Guoa, Yuxian Wanga, Zhiqiang Zhaoa, Qing Wanga, Jian Zuob(), Luyao Wanga()   

  1. a Department of Chemistry, Capital Normal University, Beijing, 100048
    b Department of Physics, Capital Normal University, Beijing, 100048
  • Received:2021-08-16 Revised:2021-09-19 Published:2022-02-24
  • Contact: Jian Zuo, Luyao Wang
  • Supported by:
    National Natural Science Foundation of China(22074095); High-Level Teachers in Beijing Municipal Universities in the Period of 13th Five Year Plan(CIT&TCD20190330)

通过使用廉价易得且易于处理的CF3SO2Na作为CF3源, 实现了操作简单的电化学氧化喹喔啉-2(1H)-酮的C—H三氟甲基化. 由于没有使用任何催化剂或氧化剂, 该方法符合绿色和可持续发展的要求. 最重要的是, 使用“电描述符图”来评估底物的反应活性, 可以清楚地看到反应/非反应边界和产量变化趋势.

关键词: 喹喔啉-2(1H)-酮, 电化学合成, 三氟甲基化, 三氟甲基亚磺酸钠, 电化学描述符

An operationally simple electrochemical oxidative C—H trifluoromethylation of quinoxalin-2(1H)-ones was achieved by employing the inexpensive, readily available and easy processing CF3SO2Na as CF3 source. In the absence of any catalysts or oxidant reagents, this method is more in line with the requirements of green and sustainable development. Most importantly, “electric-descriptor-diagram” was used to evaluate the reaction substrates. The reactive/non-reactive boundary and the trend of yield change can been clearly seen.

Key words: qinoxalin-2(1H)-ones, electrochemical synthesis, trifluoromethylation, sodium trifluoromethanesulfinate, electro-descriptors