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Direct and Oxidatively Dehydrogenative Coupling of Alcohols with Amines to Amides

Progress in Chemistry ›› 2014, Vol. 26 ›› Issue (0203) : 334 -344.

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Progress in Chemistry ›› 2014, Vol. 26 ›› Issue (0203) : 334-344 DOI: 10.7536/PC130740
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Direct and Oxidatively Dehydrogenative Coupling of Alcohols with Amines to Amides
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Abstract

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

Keywords

dehydrogenative coupling / alcohols / amines / amides / PNN-Ru complex / NHC-Ru complex / supported gold

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Ma Wenchan, Zhou Qiao, Zhang Yuecheng, Zhao Jiquan. Direct and Oxidatively Dehydrogenative Coupling of Alcohols with Amines to Amides. Progress in Chemistry, 2014, 26(0203): 334-344 DOI:10.7536/PC130740

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