Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (4): 890-895.DOI: 10.6023/cjoc201709052 Previous Articles     Next Articles



黄中寿, 朱星亮, 何云刚, 李风雷, 孟天卓, 施小新   

  1. 华东理工大学药学院 上海市化学生物学重点实验室 上海 200237
  • 收稿日期:2017-09-30 修回日期:2017-11-22 发布日期:2017-12-05
  • 通讯作者: 施小新
  • 基金资助:


Synthesis of the Variously Substituted Nitroalkenes via Ethylenediaminium Trifluoroacetate-Catalyzed Condensation of Nitroalkanes with Aryl Aldehydes

Huang Zhongshou, Zhu Xingliang, He Yungang, Li Fenglei, Meng Tianzhuo, Shi Xiaoxin   

  1. Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China
  • Received:2017-09-30 Revised:2017-11-22 Published:2017-12-05
  • Contact: 10.6023/cjoc201709052
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 20972048).

A general method for synthesis of the variously substituted nitroalkenes via ethylenediaminium trifluoroacetate (EDA-TFA)-catalyzed condensation of nitroalkanes with aryl aldehydes is described. Various aminium salts of ethylenediamine with different acids as well as aminium salts of trifluoroacetic acid with different amines were examined as catalysts, and various solvents were also tested for the reaction. It was found that EDA-TFA is obviously more effective than other aminium salts, and dimethylsulfoxide (DMSO) is better than other solvents. In presence of 5 mol% of EDA-TFA as the catalyst, one-pot reaction of aryl aldehydes with various nitroalkanes in DMSO efficiently afforded variously substituted nitroalkenes in 82%~96% yields.

Key words: aldehyde, ethylenediaminium trifluoroacetate, nitroalkanes,nitroalkenes