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2021 , Vol. 41 >Issue 3: 1216 - 1223

DOI: https://doi.org/10.6023/cjoc202009014

研究论文

聚合物氮化碳负载铜克级制备一种无需额外配体即可催化二级嘧啶-2-胺的碳-氮乌尔曼偶联反应的实用催化剂

  • 孙扬阳 ,
  • 冯刚 ,
  • 陈超 ,
  • 刘永红 ,
  • 张旭
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  • a 扬州大学化学化工学院 江苏扬州 225002
    b 江苏旅游职业学院 江苏扬州 225000

收稿日期: 2020-09-06

  修回日期: 2020-09-29

  网络出版日期: 2020-10-22

基金资助

江苏省高校优势学科资助项目

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Gram-Scale Synthesis of Polymeric Carbon Nitride-Supported Copper: A Practical Catalyst for Ullmann-Type C—N Coupling Modifying Secondary Pyrimidin-2-amines without Additional Ligand

  • Yangyang Sun ,
  • Gang Feng ,
  • Chao Chen ,
  • Yonghong Liu ,
  • Xu Zhang
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  • a School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002
    b Jiangsu College of Tourism, Yangzhou, Jiangsu 225000
* Corresponding authors. E-mail: ;

Received date: 2020-09-06

  Revised date: 2020-09-29

  Online published: 2020-10-22

Supported by

Priority Academic Program Development of Jiangsu Higher Education Institutions

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摘要

通过在550 ℃下煅烧硝酸铜与三聚氰胺前体, 可实现聚合物氮化碳负载铜(Cu/PCN)材料的克级制备. X射线光电子能谱(XPS)分析表明, 该材料中铜元素呈一价, 可在无需额外配体的条件下催化二级嘧啶-2-胺与芳卤代烃的碳-氮乌尔曼偶联反应, 以实现其氮官能团的修饰. 作为非均相催化剂, 该材料易于回收, 并可被重复使用至少五次而不失活. 该材料比传统的一价铜与钯催化剂更加活泼, 从而为制药工业合成含有嘧啶-2-胺结构的药物提供了一种高效而实用的催化剂.

关键词： 聚合物氮化碳; 铜; 催化; 碳-氮乌尔曼偶联反应; 嘧啶-2-胺

本文引用格式

孙扬阳 , 冯刚 , 陈超 , 刘永红 , 张旭 . 聚合物氮化碳负载铜克级制备一种无需额外配体即可催化二级嘧啶-2-胺的碳-氮乌尔曼偶联反应的实用催化剂[J]. 有机化学, 2021 , 41(3) : 1216 -1223 . DOI: 10.6023/cjoc202009014

Abstract

Cu/polymeric carbon nitride (PCN) can be prepared in 10 g scale by calcining Cu(NO3)2 with the melamine precursor at 550 ℃. X-ray photoelectron spectroscopy (XPS) analysis demonstrated that copper in the material was in Cu(I) form and it could catalyze the Ullmann-type C—N coupling reactions of pyrimidin-2-amine derivatives with aryl halides without additional ligand. As a heterogeneous catalyst, the material was recoverable and could be reused for at least five times without deactivation. This material was found to be even more active than traditional Cu(I) catalysts and Pd catalysts, affording an opportunity to develop the efficient and practical novel catalyst reagent for the synthesis of medicines containing pyrimidin-2-amine moieties in pharmaceutical industry.

Key words： polymeric carbon nitride (PCN); copper; catalysis; Ullmann-type C—N coupling reaction; pyrimidin-2-amine

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