Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4484-4492.DOI: 10.6023/cjoc202104039 Previous Articles     Next Articles

Special Issue: 热点论文虚拟合集



宁资慧a, 彭欣华a, 白瑞a, 刘珊珊b,*(), 李卓a, 焦林郁a,*()   

  1. a 西北大学化工学院 西安 710069
    b 陕西科技大学化学与化工学院 陕西省轻化工助剂重点实验室 西安 710021
  • 收稿日期:2021-04-18 修回日期:2021-06-30 发布日期:2021-07-19
  • 通讯作者: 刘珊珊, 焦林郁
  • 基金资助:
    国家自然科学基金(21901150); 陕西省自然科学基金(2019JQ-787)

Iridium Catalyzed C—H Amidation of Benzamides with Phosphoryl Azides in Ionic Liquids

Zihui Ninga, Xinhua Penga, Rui Baia, Shanshan Liub(), Zhuo Lia, Linyu Jiaoa()   

  1. a School of Chemical Engineering, Northwest University, Xi'an 710069
    b College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science & Technology, Xi'an 710021
  • Received:2021-04-18 Revised:2021-06-30 Published:2021-07-19
  • Contact: Shanshan Liu, Linyu Jiao
  • Supported by:
    National Natural Science Foundation of China(21901150); Natural Science Foundation of Shaanxi Province(2019JQ-787)

Phosphoramides are common structures in natural products and bioactive molecules. Additionally, they are also important intermediates in synthetic chemistry. In this paper, a direct, simple, efficient and relatively greener transition metal iridium catalyzed C—H bond amidation was reported. The target conversion was achieved in ionic liquids using weakly coordinated benzamides and phosphoryl azides as substrates and amidation reagents, respectively. Moderate to excellent isolated yields were obtained, showing good functional group tolerance and high regioselectivity. Furthermore, a possible mechanism of the reaction was proposed. The establishment of the catalytic system enriches the synthesis protocols of phosphoramides and extends the application of ionic liquids as green media in the C—H bond functionalization.

Key words: transition metal, ionic liquids, hydrocarbon activation, amidation, regioselectivity, phosphoryl azid