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2023 , Vol. 43 >Issue 2: 668 - 678

DOI: https://doi.org/10.6023/cjoc202208029

研究论文

α-氰醇甲磺酸酯与丙二酸酯的亲核取代反应合成α-芳基腈类化合物

  • 王雷刚 ,
  • 郑逸轩 ,
  • 周希 ,
  • 王海峰 ,
  • 严琼姣 ,
  • 汪伟 ,
  • 陈芬儿
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  • a 武汉工程大学药物研究院 武汉 430205
    b 复旦大学化学学院 上海 200433

收稿日期: 2022-08-23

  修回日期: 2022-10-03

  网络出版日期: 2022-11-01

基金资助

国家自然科学基金(21602144); 湖北省教育厅科研计划(Q20211503)

收起

Synthesis of α-Aryl Nitriles via Nucleophilic Substitution of α-Cyanohydrin Methanesulfonates with Malonates

  • Leigang Wang ,
  • Yixuan Zheng ,
  • Xi Zhou ,
  • Haifeng Wang ,
  • Qiongjiao Yan ,
  • Wei Wang ,
  • Fener Chen
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  • a Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
    b Department of Chemistry, Fudan University, Shanghai 200433
* Corresponding authors. E-mail: ;

Received date: 2022-08-23

  Revised date: 2022-10-03

  Online published: 2022-11-01

Supported by

National Natural Science Foundation of China(21602144); Scientific Research Project of Education Department of Hubei Province(Q20211503)

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摘要

报道了无过渡金属存在下α-氰醇甲磺酸酯与丙二酸酯的亲核取代反应. 该方法的原料廉价易得, 操作简便, 反应条件温和, 具有良好的底物适用性和官能团兼容性, 以较好的产率得到了一系列重要的丙二酸酯取代的α-芳基腈类化合物. 更重要的是, 该方法也适用于非对称的丙二酸酯和酰基酯类底物.

关键词： α-芳基腈类化合物; α-氰醇甲磺酸酯; 丙二酸酯; 亲核取代

本文引用格式

王雷刚 , 郑逸轩 , 周希 , 王海峰 , 严琼姣 , 汪伟 , 陈芬儿 . α-氰醇甲磺酸酯与丙二酸酯的亲核取代反应合成α-芳基腈类化合物[J]. 有机化学, 2023 , 43(2) : 668 -678 . DOI: 10.6023/cjoc202208029

Abstract

An efficient synthesis of α-aryl nitriles via nucleophilic substitution of α-cyanohydrin methanesulfonates with malonates is developed. This transition metal-free protocol has the advantages of cheap and easily available starting materials, mild reaction conditions, simple operation, a broad substrate scope and high functional group tolerance. Furthermore, this strategy could also be used to asymmetric malonates and acyl esters.

Key words： α-aryl nitriles; α-cyanohydrin methanesulfonates; malonates; nucleophilic substitution

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