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2025 , Vol. 45 >Issue 4: 1249 - 1260

DOI: https://doi.org/10.6023/cjoc202408005

研究论文

碱催化的β-酮腈与偶氮二甲酸酯的化学选择性取代反应

  • 郭怡诗 ,
  • 桑田 ,
  • 刘岩 ,
  • 刘平
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  • 石河子大学化学化工学院 化工绿色过程兵团重点实验室 新疆石河子 832003

收稿日期: 2024-08-06

  修回日期: 2024-10-27

  网络出版日期: 2024-11-28

基金资助

国家自然科学基金(21563025); 国家自然科学基金(22162022)

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Base-Catalyzed Chemoselective Substitution of β-Ketonitrile with Azodicarboxylates

  • Yishi Guo ,
  • Tian Sang ,
  • Yan Liu ,
  • Ping Liu
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  • Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832004
* E-mail: ;

Received date: 2024-08-06

  Revised date: 2024-10-27

  Online published: 2024-11-28

Supported by

National Natural Science Foundation of China(21563025); National Natural Science Foundation of China(22162022)

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摘要

开发了β-酮腈与偶氮二甲酸酯的碱催化C—N偶联反应. 在Et3N催化下, 高选择性地得到了一系列二取代的 C—N偶联产物, 收率从良好到优秀. 在K2CO3催化下进行的单取代C—N键形成反应也得到了新型烯醇基目标产物. 该方法简单温和, 化学选择性高, 底物相容性好, 可容忍多种官能团, 并实现了克级规模的合成. 该反应是一个亲核取代过程, 没有自由基的参与.

关键词： 碱催化; β-酮腈; 选择性取代; 偶氮二甲酸酯

本文引用格式

郭怡诗 , 桑田 , 刘岩 , 刘平 . 碱催化的β-酮腈与偶氮二甲酸酯的化学选择性取代反应[J]. 有机化学, 2025 , 45(4) : 1249 -1260 . DOI: 10.6023/cjoc202408005

Abstract

Base-catalyzed nucleophilic substitution reactions of β-ketonitrile with azodicarboxylates have been developed. A series of disubstituted C—N coupling products were obtained in good to excellent yields under Et3N catalysis. Monosubstitution C—N bond formation reaction catalyzed by K2CO3 also gave novel enol-based target products. This method is simple and mild, with good chemoselectivity, excellent substrate compatibility and tolerance for various functional groups, and achieves gram-scale synthesis. The reaction is a nucleophilic substitution process without the involvement of free radicals.

Key words： base-catalysis; β-ketonitrile; selective substitution; azodicarboxylate

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