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2024 , Vol. 44 >Issue 3: 940 - 950

DOI: https://doi.org/10.6023/cjoc202401002

研究论文

电化学促进2,2,6,6-四甲基哌啶氧化物(TEMPO)介导的甘氨酸衍生物氧化脱氢Povarov/串联反应

  • 李章健 ,
  • 王振华 ,
  • 郭剑峰 ,
  • 方萍 ,
  • 马聪 ,
  • 刘润华 ,
  • 梅天胜
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  • a 四川师范大学化学与材料科学学院 成都 610068
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 中国科学院大学 上海 200032
    c 中国科学院上海有机化学研究所 宁波中科新材料创制中心 浙江宁波 315800

收稿日期: 2024-01-04

  修回日期: 2024-02-28

  网络出版日期: 2024-03-05

基金资助

中国科学院战略性先导科技专项(XDB0610000); 国家重点研发项目(2021YFA1500100); 国家自然科学基金(21821002); 国家自然科学基金(91956112); 国家自然科学基金(22101294); 上海市科学技术委员会(21ZR1476500); 上海市科学技术委员会(20XD1425100); 宁波市自然科学基金(2023J035)

收起

Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives

  • Zhang-Jian Li ,
  • Zhen-Hua Wang ,
  • Jian-Feng Guo ,
  • Ping Fang ,
  • Cong Ma ,
  • Run-Hua Liu ,
  • Tian-Sheng Mei
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  • a College of Chemistry and Materials, Sichuan Normal University, Chengdu 610068
    b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032
    c Ningbo Zhongke Creation Center of New Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Ningbo, Zhejiang 315800
*E-mail: ;
;

Received date: 2024-01-04

  Revised date: 2024-02-28

  Online published: 2024-03-05

Supported by

Strategic Priority Research Program of the Chinese Academy of Sciences(XDB0610000); National Key R&D Program of China(2021YFA1500100); National Natural Science Foundation of China(21821002); National Natural Science Foundation of China(91956112); National Natural Science Foundation of China(22101294); Science and Technology Commission of Shanghai Municipality of Shanghai(21ZR1476500); Science and Technology Commission of Shanghai Municipality of Shanghai(20XD1425100); Natural Science Foundation of Ningbo(2023J035)

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摘要

研究了电化学氧化甘氨酸衍生物与烯烃之间的氧化脱氢Povarov/串联反应, 其中氮氧自由基2,2,6,6-四甲基哌啶氧化物(TEMPO)作为媒介降低了电化学反应的电位, 避免了某些富电子的芳胺在较高电位下的过氧化. 它为甘氨酸衍生物的氮-α位官能团化提供了潜在的途径, 并通过Shono氧化与Povarov反应的结合, 开发了一种在温和条件下高产率合成喹啉衍生物的有效方法.

关键词： 电化学; 2,2,6,6-四甲基哌啶氧化物(TEMPO); Povarov反应; Shono氧化

本文引用格式

李章健 , 王振华 , 郭剑峰 , 方萍 , 马聪 , 刘润华 , 梅天胜 . 电化学促进2,2,6,6-四甲基哌啶氧化物(TEMPO)介导的甘氨酸衍生物氧化脱氢Povarov/串联反应[J]. 有机化学, 2024 , 44(3) : 940 -950 . DOI: 10.6023/cjoc202401002

Abstract

The oxidative dehydrogenation Povarov/tandem reaction between electrochemically oxidized glycine derivatives and olefins was investigated. Specifically, a nitrogen oxide radical 2,2,6,6-tetramethylpiperidoxyl (TEMPO) was used as a redox mediator to reduce the potential of the electrochemical reaction and avoid over-oxidation of electron-rich aromatic amines at higher potentials. The reaction provides a potential pathway for the nitrogen-α functionalization of glycine derivatives. Further, the reaction represents an efficient method for synthesizing quinoline derivatives under mild conditions to achieve high yields through a combination of Shono oxidation and Povarov reactions.

Key words： electrochemistry; 2,2,6,6-tetramethylpiperidoxyl (TEMPO); Povarov reaction; Shono oxidation

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