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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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: ;
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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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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

Cite this article

Zhang-Jian Li , Zhen-Hua Wang , Jian-Feng Guo , Ping Fang , Cong Ma , Run-Hua Liu , Tian-Sheng Mei . Electrochemistry-Enabled 2,2,6,6-Tetramethylpiperidoxyl (TEMPO)-Mediated Oxidative Dehydrogenation Povarov/Tandem Reactions of Glycine Derivatives[J]. Chinese Journal of Organic Chemistry, 2024 , 44(3) : 940 -950 . DOI: 10.6023/cjoc202401002

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