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化学进展 2014, Vol. 26 Issue (0203): 334-344 DOI: 10.7536/PC130740 前一篇   后一篇

• 综述与评论 •

醇-胺直接脱氢及氧化脱氢偶联酰胺化反应

马文婵, 周乔, 张月成, 赵继全*   

  1. 河北工业大学化工学院 天津 300130
  • 收稿日期:2013-07-01 修回日期:2013-09-01 出版日期:2014-02-15 发布日期:2013-12-18
  • 通讯作者: 赵继全，e-mail：zhaojq@hebut.edu.cn E-mail:zhaojq@hebut.edu.cn
  • 基金资助:

    国家自然科学基金项目（No.21276061）和河北省自然科学基金项目（No.B2013202158）资助

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Direct and Oxidatively Dehydrogenative Coupling of Alcohols with Amines to Amides

Ma Wenchan, Zhou Qiao, Zhang Yuecheng, Zhao Jiquan*   

  1. School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, China
  • Received:2013-07-01 Revised:2013-09-01 Online:2014-02-15 Published:2013-12-18
  • Supported by:

    The work was supported by the National Natural Science Foundation of China (No.21276061) and the Natural Science Foundation of Hebei Province, China (No.B2013202158)

醇-胺（氨）直接脱氢及氧化脱氢偶联生成酰胺具有原子经济性高和对环境友好等优点，因而受到广泛关注。研究发现，一些过渡金属钌及铑配合物、负载金及银纳米粒子、氧化锰分子筛（OMS-2）以及基于铜、铁化合物的催化体系在醇-胺（氨）直接脱氢或氧化脱氢偶联生成酰胺反应中显示出优良的催化性能。本文首先介绍了PNN-钌、NHC-钌配合物、铑配合物以及负载银原子簇催化的醇-胺（氨）直接脱氢偶联生成酰胺反应的研究进展，然后对负载纳米金粒子、氧化锰分子筛（OMS-2）以及基于铜、铁化合物的催化体系催化的不同氧化剂，包括分子氧、叔丁基过氧化氢以及分子碘氧化的氧化酰胺化反应进行了总结。对各催化剂或催化体系的适用范围和优缺点进行了分析，阐述了主要催化剂或催化体系的催化机理。此外，还对无过渡金属参与的醇-胺氧化酰胺化反应体系进行概述。最后，在总结现有成果的基础上指出了该领域的发展方向。

关键词： 脱氢偶联, 醇, 胺, 酰胺, PNN-Ru配合物, NHC-Ru配合物, 负载金

Direct and oxidatively dehydrogenative coupling of alcohols with amines or ammonia to amides have the advantages of high atom economy and environmental friendliness, therefore,they have received much attention from scientists. They have been found that some ruthenium and rhodium complexes, supported gold and silver nanoparticles, manganese oxide based molecular sieves (OMS-2), and copper and iron-based catalytic systems have exhibited excellent performances on the amidation reactions. In this article, the progress of direct dehydrogenative coupling of alcohols with amines or ammonia to amides respectively catalyzed by ruthenium and rhodium complexes, supported gold and silver nanoparticles is introduced firstly. Then the oxidative amidation reactions of alcohols with amines or ammonia respectively catalyzed by supported gold nanoparticles, manganese oxide based molecular sieves (OMS-2), and copper and iron-based catalytic systems with different reagents, including molecular oxygen, tert-butyl peroxide (TBHP) and molecular iodine as oxidants are reviewed. The possible catalytic mechanisms of some catalysts or catalytic systems are discussed. Meanwhile, the scope of application, advantages and disadvantages of each catalyst or catalytic system are described. In addition, some transition metal-free reaction systems for the oxidative amidation of alcohols with amines are also summarized. Finally, the development directions in this field are predicted based on the results described above.

Contents
1 Introduction
2 Direct dehydrogenative coupling of alcohols with amines to amides
2.1 Ruthenium and rhodium complexes as homogeneous catalysts for the reaction
2.2 Supported gold and silver as heterogeneous catalysts for the reaction
3 Oxidative amidation of alcohols with amines
3.1 Oxidative amidation of alcohols with amines by molecular oxygen
3.2 Oxidative amidation of alcohols with amines by other oxidants
4 Conclusions

Key words: dehydrogenative coupling, alcohols, amines, amides, PNN-Ru complex, NHC-Ru complex, supported gold

中图分类号: 

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