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研究论文

以NH4+/DMF组合为氰源,Ag/Cu介导芳基羧酸的氧化脱羧氰化反应

付拯江a,b, 郝广果a, 石泉清a, 周金琪a, 姜李高a, 汪水亮a, 郭生梅a, 蔡琥a   

  1. a 南昌大学化学学院 南昌 330031;
    b 南京大学配位化学国家重点实验室 南京 210023
  • 收稿日期:2020-06-17 修回日期:2020-07-27 出版日期:2030-01-01 发布日期:2020-08-27
  • 通讯作者: 付拯江, 蔡琥 E-mail:fuzhengjiang@ncu.edu.cn;caihu@ncu.edu.cn
  • 基金资助:
    国家自然科学基金(No.21761021和21861026)资助项目,江西省教学改革项目(No.JXJG-18-1-56)和南昌大学科研训练项目(No.3664)

Ag/Cu-Mediated Aerobic Decarboxylative Cyanation of Arene Carboxylic Acids Using Ammonium and DMF as a Combined Cyanide Source

Fu Zhengjianga,b, Hao Guangguoa, Shi Quanqinga, Zhou Jinqia, Jiang Ligaoa, Wang Shuilianga, Guo Shengmeia, Cai Hua   

  1. a College of Chemistry, Nanchang University, Nanchang 330031;
    b State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023
  • Received:2020-06-17 Revised:2020-07-27 Online:2030-01-01 Published:2020-08-27
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21761021 and 21861026) and Project of Teaching Reform in Colleges and Universities of Jiangxi Province (No. JXJG-18-1-56) and Scientific Research and Training Program of Nanchang University (No. 3664)

有氧条件下,以NH4OAC/DMF组合为氰源,发展了Ag/Cu介导芳基羧酸脱羧的氰化反应,并进一步实现了以该方法为关键步骤的吡仑帕奈(perampanel)合成。初步的机理研究表明,产物中的“CN”来源于NH4+/DMF组合;催化体系中的Cu决定着反应的发生,而Ag有利于反应的转化。

关键词: 脱羧, 芳基腈化物, 有氧条件

A Ag/Cu-mediated decarboxylative cyanation of aryl carboxylic acids has been well established using NH4OAC/DMF as a combined cyanide source under aerobic conditions, and the synthesis of perampanel was further realized with this method as the key step. Preliminary mechanistic investigation indicated the "CN" of desired products was from the combination of DMF and ammonia; Cu in the catalytic system was essential for the process, whereas Ag was beneficial for the transformation.

Key words: Decarboxylation, Aryl nitriles, Aerobic conditions