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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 8: 2418 - 2427

DOI: https://doi.org/10.6023/cjoc202204039

ARTICLES

Ruthenium Complex-Catalyzed Tandem Reactions of Alcohols with Acetonitriles for Synthesis of α-Substituted Amides

  • Mei Wang ,
  • Huihua Gong ,
  • Haiyan Fu ,
  • Xueli Zheng ,
  • Hua Chen ,
  • Ruixiang Li
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  • College of Chemistry, Sichuan University, Chengdu 641400
* E-mail:

Received date: 2022-04-15

  Revised date: 2022-05-24

  Online published: 2022-05-27

Supported by

National Natural Science Foundation of China(21572137)

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Abstract

A ruthenium complex-catalyzed tandem reaction of alcohols with nitriles in one pot has been developed, providing a green and atom-economic synthetic method of α-substituted amide. This method features high reactivity, high selectivity and good substrate compatibility. Good to high yields are obtained for most substrates and the highest yield is 96%. Mechanistic studies reveal that the alcohol first undergoes an acceptorless dehydrogenation into aldehyde. the resulting aldehyde occurs a nucleophilic addition with the α-position carbon of phenylacetonitrile to form α,β-unsaturated nitrile and water. Subsequently, the unsaturated nitrile is hydrogenated with ruthenium-hydride species formed by the dehydrogenation of alcohol to give saturated nitrile, and then the water, generated by the nucleophilic addition, causes the catalytic hydrolysis of cyano group to finally generate α-arylamide.

Key words： ruthenium complex; alcohol; nitrile; α-arylamide

Cite this article

Mei Wang , Huihua Gong , Haiyan Fu , Xueli Zheng , Hua Chen , Ruixiang Li . Ruthenium Complex-Catalyzed Tandem Reactions of Alcohols with Acetonitriles for Synthesis of α-Substituted Amides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2418 -2427 . DOI: 10.6023/cjoc202204039

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