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2023 , Vol. 43 >Issue 5: 1875 - 1882

DOI: https://doi.org/10.6023/cjoc202302016

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
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  • 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

  网络出版日期: 2023-04-14

基金资助

国家自然科学基金(22071217); 国家自然科学基金(91956117)

收起

Nickel-Catalyzed Intramolecular Dearomative Arylation of Pyridiniums and Quinoliniums

  • Jun Lu ,
  • Qichuang Li ,
  • Renxiao Liang ,
  • Yixia Jia
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  • College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
* Corresponding author. E-mail:

Received date: 2023-02-14

  Revised date: 2023-04-03

  Online published: 2023-04-14

Supported by

National Natural Science Foundation of China(22071217); National Natural Science Foundation of China(91956117)

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摘要

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; 镍

本文引用格式

芦军 , 李奇闯 , 梁仁校 , 贾义霞 . 镍催化吡啶/喹啉鎓盐分子内去芳构化芳基加成反应[J]. 有机化学, 2023 , 43(5) : 1875 -1882 . DOI: 10.6023/cjoc202302016

Abstract

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

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