有机化学 ›› 2023, Vol. 43 ›› Issue (5): 1875-1882.DOI: 10.6023/cjoc202302016 上一篇    下一篇

所属专题: 有机硼化学专辑

研究论文

镍催化吡啶/喹啉鎓盐分子内去芳构化芳基加成反应

芦军, 李奇闯, 梁仁校, 贾义霞*()   

  1. 浙江工业大学化工学院 杭州 310014
  • 收稿日期:2023-02-14 修回日期:2023-04-03 发布日期:2023-04-13
  • 通讯作者: 贾义霞
  • 基金资助:
    国家自然科学基金(22071217); 国家自然科学基金(91956117)

Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums

Jun Lu, Qichuang Li, Renxiao Liang, Yixia Jia()   

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
  • Received:2023-02-14 Revised:2023-04-03 Published:2023-04-13
  • Contact: Yixia Jia
  • Supported by:
    National Natural Science Foundation of China(22071217); National Natural Science Foundation of China(91956117)

发展了溴化镍催化下吡啶/喹啉鎓盐与溴代芳烃的分子内去芳构化加成反应. 在锌粉作还原剂条件下, 镍催化的溴代芳烃与吡啶/喹啉鎓盐碳氮双键的分子内Grignard型加成反应顺利发生, 实现了吡啶/喹啉的去芳构化, 并以中等至良好的收率合成了一系列具有二氢吡啶/二氢喹啉结构单元的螺环吲哚酮类化合物.

关键词: 吡啶, 喹啉, 芳基化, 去芳构化,

A nickel-catalyzed intramolecular dearomative arylation reaction of pyridiniums and quinoliniums is developed. In the presence of zinc powder as a reducing agent, the intramolecular Grignard-type addition of arylbromides to the C=N bonds of pyridiniums and quinoliniums proceeds smoothly to render pyridines and quinolines dearomatization, leading to a range of spirooxindole derivatives bearing dihydropyridine and dihydroquinoline moieties in moderate to good yields.

Key words: pyridine, quinoline, arylation, dearomatization, nickel