Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(4): 890-895. doi: 10.6023/cjoc201709052 shu

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

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

Corresponding author: Shi Xiaoxin, xxshi@ecust.edu.cn
Received Date: 30 September 2017
Revised Date: 22 November 2017
Available Online: 5 April 2017
Fund Project: the National Natural Science Foundation of China 20972048Project supported by the National Natural Science Foundation of China (No. 20972048)

Figures(1)

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.
- aldehyde,
- ethylenediaminium trifluoroacetate,
- nitroalkanes,
- nitroalkenes
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