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

doi:10.6023/cjoc201709052

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

Articles

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

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 E-mail:xxshi@ecust.edu.cn
基金资助:
国家自然科学基金（No.20972048）资助项目.

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

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 E-mail:xxshi@ecust.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20972048).

1. Synthesis of the Variously Substituted Nitroalkenes via Ethylenediaminium Trifluoroacetate-Catalyzed Condensation of Nitroalkanes with Aryl Aldehydes.PDF(897KB)

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

Cite this article

Huang Zhongshou, Zhu Xingliang, He Yungang, Li Fenglei, Meng Tianzhuo, Shi Xiaoxin. Synthesis of the Variously Substituted Nitroalkenes via Ethylenediaminium Trifluoroacetate-Catalyzed Condensation of Nitroalkanes with Aryl Aldehydes[J]. Chin. J. Org. Chem., 2018, 38(4): 890-895.

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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

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

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