Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (1): 200-207.DOI: 10.6023/cjoc202106012 Previous Articles     Next Articles



刘锐凯, 许峥, 宁志涛, 杜正银*()   

  1. 西北师范大学化学化工学院 兰州 730070
  • 收稿日期:2021-06-06 修回日期:2021-08-11 发布日期:2021-09-08
  • 通讯作者: 杜正银
  • 基金资助:
    国家自然科学基金(21262028); 国家自然科学基金(21762039); 甘肃省自然科学基金(20JR5RA521)

Synthesis of β-Sulfonyl Enamines via Iodine-Catalyzed Reaction between Vinyl Azides and Sodium Arylsulfinates

Ruikai Liu, Zheng Xu, Zhitao Ning, Zhengyin Du()   

  1. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2021-06-06 Revised:2021-08-11 Published:2021-09-08
  • Contact: Zhengyin Du
  • Supported by:
    National Natural Science Foundation of China(21262028); National Natural Science Foundation of China(21762039); Natural Science Foundation of Gansu Province(20JR5RA521)

The present protocol provides the facile and highly efficient synthesis of various Z-structure N-unprotected β-sulfonyl enamine compounds in a manner by using inexpensive molecular iodine as catalyst, vinyl azides as free radical acceptor, and sodium arylsulfinates as free radical sources. In this reaction, ethanol was used as solvent and bistrifluoromethanesulfonimide (Tf2NH) was used as additive. The reaction was carried out at 40 ℃ for 4~6 h to obtain β-sulfonyl enamine compounds with good yields. The method does not need to use metal catalyst, and has the advantages of simple conditions, short reaction time and wide substrate application range.

Key words: iodine catalysis, vinyl azide, free radical addition, sulfonyl enamine