Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1341-1364.DOI: 10.6023/cjoc202209007 Previous Articles     Next Articles



缪存静a, 姚佳琪b,*()   

  1. a 浙江大学医学院附属邵逸夫医院钱塘院区药学部 杭州 310018
    b 中国科学院大学宁波华美医院药学部 浙江宁波 315000
  • 收稿日期:2022-09-05 修回日期:2022-10-17 发布日期:2022-11-21
  • 通讯作者: 姚佳琪

Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage

Cunjing Miaoa, Jiaqi Yaob()   

  1. a Department of Pharmacy, Qiantang Campus, Sir Run Run Shaw Hospital, College of Medicine, Zhejiang University, Hangzhou, 310018
    b Department of Pharmacy, Ningbo Huamei Hospital, University of Chinese Academy of Sciences, Ningbo, Zhejiang, 315000
  • Received:2022-09-05 Revised:2022-10-17 Published:2022-11-21
  • Contact: Jiaqi Yao

Aromatic nitriles are one of the ubiquitous versatile materials in organic synthesis, and also a class of important synthetic intermediates for a wide range of applications in pharmaceuticals, agricultural chemicals, dyes, spices, and functional materials. However, the C—CN bond of aryl nitriles has rarely been considered as a valuable reaction site due to the high thermodynamic stability. Therefore, the development of simple and efficient methods to catalyze the C—CN bond transformation of aryl nitriles has become one of the hot research topics in recent years. In this review, the recent advances in the transformation reactions of aromatic nitriles via C—CN bond cleavage in the past decade are summarized and classified according to different reaction mechanisms, mainly including transition metal-mediated/catalyzed C—CN transformation, free radical-mediated C—CN transformation, Lewis acid, base or Brønsted acid-mediated C—CN transformation. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail.

Key words: aromatic nitriles, C—CN bond cleavage, transformation reaction, classification of reaction mechanisms