Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (7): 1864-1869.DOI: 10.6023/cjoc201701012 Previous Articles     Next Articles



蔺松波a, 何兴瑞a, 孟金鹏a, 顾海宁a, 张培志b, 吴军a   

  1. a. 浙江大学化学系 杭州 310027;
    b. 浙江科技学院生物与化学工程学院 杭州 310012
  • 收稿日期:2017-01-05 修回日期:2017-02-25 发布日期:2017-03-03
  • 通讯作者: 吴军
  • 基金资助:


Transition-Metal-Free Synthesis of o-Halodiarylamines from o-Halophenols

Lin Songboa, He Xingruia, Meng Jinpenga, Gu Haininga, Zhang Peizhib, Wu Juna   

  1. a. Department of Chemistry, Zhejiang University, Hangzhou 310027;
    b. School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310012
  • Received:2017-01-05 Revised:2017-02-25 Published:2017-03-03
  • Contact: 10.6023/cjoc201701012
  • Supported by:

    Project supported by the Special Fund for Agro-scientific Research in the Public Interest (No.201403030) and the National Natural Science Foundation of China (No.31471807).

A metal-free method (KOH/DMSO) for the synthesis of o-halodiarylamines from o-halophenols and 2-bromo-N-arylpropanamide via Smiles rearrangement reaction as a key step has been developed in this paper. This method has advantages of simple and efficient operation, easy available starting materials and transition-metal-free conditions. It exhibits the certain application value. Using this method, a series of o-halodiarylamines have been synthesized in 23%~81% yields.

Key words: transition-metal-free reaction, o-halophenols, o-halodiarylamines, Smiles rearrangement reaction