Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2418-2427.DOI: 10.6023/cjoc202204039 Previous Articles     Next Articles



王梅, 龚慧华, 付海燕, 郑学丽, 陈华, 李瑞祥*()   

  1. 四川大学化学学院 成都 610064
  • 收稿日期:2022-04-15 修回日期:2022-05-24 发布日期:2022-05-27
  • 通讯作者: 李瑞祥
  • 基金资助:

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()   

  1. College of Chemistry, Sichuan University, Chengdu 641400
  • Received:2022-04-15 Revised:2022-05-24 Published:2022-05-27
  • Contact: Ruixiang Li
  • Supported by:
    National Natural Science Foundation of China(21572137)

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