有机化学 ›› 2024, Vol. 44 ›› Issue (3): 1021-1030.DOI: 10.6023/cjoc202307002 上一篇    下一篇

研究论文

亚硝基苯参与的电化学串联环化反应构建喹啉/吡咯

杨帆a, 方婷b, 杨桂春a, 高梦a,*()   

  1. a 湖北大学化学化工学院 有机功能分子合成与应用教育部重点实验室 武汉 430062
    b 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2023-07-03 修回日期:2023-08-16 发布日期:2024-04-02
  • 基金资助:
    国家自然科学基金(22271085)

Electrochemical Cascade Cyclization Reactions of Nitrosobenzenes in Construction of Quinolines and Pyrroles

Fan Yanga, Ting Fangb, Guichun Yanga, Meng Gaoa()   

  1. a Ministry-of-Education Key Laboratory for the Synthesis and Application of Organic Functional Molecule, School of Chemistry and Chemical Engineering, Hubei University, Wuhan 430062
    b College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072
  • Received:2023-07-03 Revised:2023-08-16 Published:2024-04-02
  • Contact: *E-mail: drmenggao@163.com
  • Supported by:
    National Natural Science Foundation of China(22271085)

报道了一种多取代喹啉/吡咯杂环化合物的电化学合成新方法. 反应以亚硝基苯和贫电子内炔为起始物, 在无需额外金属催化剂、室温条件下, 通过阴极单电子还原的策略, 选择性地还原亚硝基苯产生亚硝基自由基, 随后与炔烃进行串联环化反应, 绿色、高效地合成了一系列具有高附加值的多取代喹啉/吡咯杂环化合物.

关键词: 电化学合成, 串联环化, 亚硝基苯

A novel electrochemical cascade cyclization between nitrosobenzene and electron-deficient alkynes was developed in this work. The use of electroreduction for the activation of nitrosobenzene which highlighted the unique possibilities associated with electrochemical activation methods. This protocol represents a simple, efficient, and environmentally benign way to construct substituted quinolines and pyrroles in good yields with high selectivity.

Key words: electrosynthesis, cascade cyclization, nitrosobenzene