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2018 , Vol. 38 >Issue 4: 890 - 895

DOI: https://doi.org/10.6023/cjoc201709052

研究论文

乙二胺三氟乙酸盐催化硝基烷烃与芳香醛缩合制备各种取代的硝基烯烃

  • 黄中寿 ,
  • 朱星亮 ,
  • 何云刚 ,
  • 李风雷 ,
  • 孟天卓 ,
  • 施小新
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  • 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

  网络出版日期: 2017-12-05

基金资助

国家自然科学基金（No.20972048）资助项目.

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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
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  • Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China

Received date: 2017-09-30

  Revised date: 2017-11-22

  Online published: 2017-12-05

Supported by

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

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摘要

描述了乙二胺三氟乙酸盐（EDA-TFA）催化硝基烷烃与芳香醛缩合制备各种取代硝基烯烃的通用方法.文中考察了乙二胺与各种酸的铵盐以及三氟乙酸与各种胺的铵盐对醛与硝基烷烃缩合反应的催化性能，并考察了不同溶剂对反应的影响，研究发现乙二胺三氟乙酸盐（EDA-TFA）催化能力相对较强，二甲基亚砜（DMSO）作溶剂反应收率较高.在5 mol%的EDA-TFA作催化剂以及DMSO作溶剂情况下，硝基烷烃与芳香醛进行"一锅法"缩合反应，以82%~96%高收率得到各种取代的硝基烯烃.

关键词： 醛; 乙二胺三氟乙酸盐; 硝基烷烃; 硝基烯烃

本文引用格式

黄中寿 , 朱星亮 , 何云刚 , 李风雷 , 孟天卓 , 施小新 . 乙二胺三氟乙酸盐催化硝基烷烃与芳香醛缩合制备各种取代的硝基烯烃[J]. 有机化学, 2018 , 38(4) : 890 -895 . DOI: 10.6023/cjoc201709052

Abstract

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

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