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2021 , Vol. 41 >Issue 8: 3223 - 3234

DOI: https://doi.org/10.6023/cjoc202103049

研究论文

无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应

  • 高君青 ,
  • 翁信军 ,
  • 马聪 ,
  • 徐学涛 ,
  • 方萍 ,
  • 梅天胜
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  • a 五邑大学生物科技与大健康学院 广东江门 529020
    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 分子合成卓越中心 上海 200032
† 共同第一作者

收稿日期: 2021-03-26

  修回日期: 2021-04-26

  网络出版日期: 2021-05-14

基金资助

国家自然科学基金(21772222); 国家自然科学基金(21821002); 广东省教育厅基金(2017KSYS010); 广东省教育厅基金(2017KZDXM084); 广东省教育厅基金(2019KZDZX2003); 广东省教育厅基金(2019KZDXM035)

收起

Electrochemical 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO)-Mediated α-Cyanation and Phosphonylation of Cyclic Amines with Metal-Free Conditions

  • Junqing Gao ,
  • Xinjun Weng ,
  • Cong Ma ,
  • Xuetao Xu ,
  • Ping Fang ,
  • Tiansheng Mei
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  • a School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
    b Center for Excellence in Molecular Synthesis, State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
† (These authors contributed equally to this work).
*Corresponding authors.E-mail: ;
E-mail: ;
E-mail:

Received date: 2021-03-26

  Revised date: 2021-04-26

  Online published: 2021-05-14

Supported by

National Natural Science Foundation of China(21772222); National Natural Science Foundation of China(21821002); Department of Education of Guangdong Province(2017KSYS010); Department of Education of Guangdong Province(2017KZDXM084); Department of Education of Guangdong Province(2019KZDZX2003); Department of Education of Guangdong Province(2019KZDXM035)

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摘要

探究了无金属电化学氧化氰化和膦酸酯基化反应, 其中2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)降低了底物的电极电位, 避免了某些富电子芳香胺在电化学条件下的过氧化反应. 该方法具有良好的官能团兼容性, 是在温和条件下合成α-氨基腈和α-氨基膦酸酯的一种有效且实用的方法, 通过研究表明产物通过Shono氧化形成亚胺物种来实现的.

关键词： 电化学; Shono氧化; 氰基化; 膦酸酯基化

本文引用格式

高君青 , 翁信军 , 马聪 , 徐学涛 , 方萍 , 梅天胜 . 无金属参与的电化学促进2,2,6,6-四甲基哌啶-氮-氧化物(TEMPO)介导的环胺α-氰化和膦酰化反应[J]. 有机化学, 2021 , 41(8) : 3223 -3234 . DOI: 10.6023/cjoc202103049

Abstract

Metal-free electrochemical oxidation cyanation and phosphonylation reactions had been developed, in which 2,2,6,6-tetramethylpiperidinyl-N-oxyl (TEMPO) reduced the electrode potential of substrate and avoided over oxidation of some electron rich aromatic amines under electrochemical conditions. This protocol had good functional group compatibility, which made it to be a practical and efficient method to synthesize α-aminonitriles and α-amino phosphonates under mild conditions. Preliminary study indicated that the formation of the product was through the Shono oxidation of imine species.

Key words： electrochemistry; Shono oxidation; cyanation; phosphonylation

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