Citation: Liu Boyu, Xu Xianjun, Huang Liliang, Feng Huangdi. One-Pot Synthesis of Unsymmetrical 1, 4-Diaminobutynes by Cu(I)-Catalyzed Cross-Coupling of Propiolic Acid, Secondary Amine, Aldehydes and Formaldehyde[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1290-1296. doi: 10.6023/cjoc201911020 shu

One-Pot Synthesis of Unsymmetrical 1, 4-Diaminobutynes by Cu(I)-Catalyzed Cross-Coupling of Propiolic Acid, Secondary Amine, Aldehydes and Formaldehyde

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620

Corresponding author: Huang Liliang, llhuang999@126.com Feng Huangdi, hdfeng@sues.edu.cn
Received Date: 12 November 2019
Revised Date: 21 January 2020
Available Online: 23 February 2020
Fund Project: the Natural Science Foundation of Shanghai City 15ZR1418800Project supported by the Natural Science Foundation of Shanghai City (No. 15ZR1418800), the China Postdoctoral Science Foundation (No. 2016M601681), and the Shanghai University of Engineering Science (Nos. cs1704006, 201810856017)the China Postdoctoral Science Foundation 2016M601681the Shanghai University of Engineering Science 201810856017the Shanghai University of Engineering Science cs1704006

Figures(3)

A highly selective and efficient copper-catalyzed sequential approach for the one-pot two-step synthesis of unsymmetrical 1, 4-diamino-2-butynes from propiolic acid, secondary alkylamine, aldehyde and formaldehyde solution has been developed. The process of this reaction was involved in the generation of key intermediate propargylamines which were obtained via decarboxylative A³-coupling reaction. After that, the intermediate propargylamines would react with in situ formed iminium ions to give the cross-coupling target products in moderate to excellent yields under microwave irradiation.
- unsymmetrical diaminobutynes,
- decarboxylative coupling,
- A³-coupling,
- cross-coupling,
- copper-catalyzed
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