Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 688-694.DOI: 10.6023/cjoc202008018 Previous Articles     Next Articles

Article

三聚氯氰催化及溶剂效应实现温和高效的酮肟贝克曼重排反应

周婷婷1, 刘霞1, 叶子航1, 周奕鹏1, 杨雅淇1, 徐清1,*()   

  1. 1 温州大学化学与材料工程学院 浙江温州 325035
  • 收稿日期:2020-08-12 修回日期:2020-09-18 发布日期:2020-09-30
  • 通讯作者: 徐清
  • 作者简介:
    * Corresponding author. E-mail: qing-xu@wzu.edu.cn
  • 基金资助:
    国家自然科学基金(21672163); 浙江省自然科学基金杰出青年基金(LR14B020002)

Cyanuric Chloride Catalysis and Solvent Effect Leading to a Mild and Efficient Beckmann Rearrangement of Ketoximes

Tingting Zhou1, Xia Liu1, Zihang Ye1, Yipeng Zhou1, Yaqi Yang1, Qing Xu1,*()   

  1. 1 College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035
  • Received:2020-08-12 Revised:2020-09-18 Published:2020-09-30
  • Contact: Qing Xu
  • Supported by:
    the National Natural Science Foundation of China(21672163); the Natural Science Foundation of Zhejiang Province for Distinguished Young Scholars(LR14B020002)

By using hexafluoroisopropanol as the solvent, a low loading of cyanuric chloride could effectively catalyze the Beckmann rearrangement of ketoximes to obtain the corresponding amide products under mild conditions, such as room temperature and air atmosphere. The effect of hexafluoroisopropanol was greatly different from that of other solvents. This method has the advantages of simple operation, low catalyst loading, recoverability of solvent, mild conditions, good tolerance of the functional groups, broad substrate scope and high product yields. It is a relatively green and practical method for the preparation of amide compounds.

Key words: ketoxime, Beckmann rearrangement, cyanuric chloride, hexafluoroisopropanol, mild condition, amide