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  

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

作　　者：李章健 王振华 郭剑峰 方萍 马聪 刘润华 梅天胜 Li Zhang-Jian;Wang Zhen-Hua;Guo Jian-Feng;Fang Ping;Ma Cong;Liu Run-Hua;Mei Tian-Sheng(College of Chemistry and Materials,Sichuan Normal University,Chengdu 610068;State Key Laboratory of Organometallic Chemistry,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai 200032;Ningbo Zhongke Creation Center of New Materials,Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Ningbo,Zhejiang 315800)

机构地区：[1]四川师范大学化学与材料科学学院,成都610068 [2]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 [3]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

出　　处：《有机化学》2024年第3期940-950,共11页Chinese Journal of Organic Chemistry

基　　金：Project supported by the Strategic Priority Research Program of the Chinese Academy of Sciences(No.XDB0610000);the National Key R&D Program of China(No.2021YFA1500100);the National Natural Science Foundation of China(Nos.21821002,91956112,22101294);the Science and Technology Commission of Shanghai Municipality of Shanghai(Nos.21ZR1476500,20XD1425100);the Natural Science Foundation of Ningbo(No.2023J035)。

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.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-αfunctionalization 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.

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 

分 类 号：O626.323[理学—有机化学]