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

doi:10.6023/cjoc201911020

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1290-1296.DOI: 10.6023/cjoc201911020 Previous Articles Next Articles

铜(I)催化丙炔酸、仲胺、醛和甲醛一锅法交叉偶联构建非对称1,4-二氨基丁炔

刘博瑜, 徐仙君, 黄立梁, 冯煌迪

上海工程技术大学化学化工学院上海 201620

收稿日期:2019-11-12 修回日期:2020-01-21 发布日期:2020-03-04
通讯作者: 黄立梁, 冯煌迪 E-mail:hdfeng@sues.edu.cn;llhuang999@126.com
基金资助:
上海市自然科学基金（No.15ZR1418800）、中国博士后科学基金（No.2016M601681）、上海工程技术大学（Nos.cs1704006，201810856017）.

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

Liu Boyu, Xu Xianjun, Huang Liliang, Feng Huangdi

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

Received:2019-11-12 Revised:2020-01-21 Published:2020-03-04
Supported by:
Project 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).

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Abstract

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.

Key words: unsymmetrical diaminobutynes, decarboxylative coupling, A³-coupling, cross-coupling, copper-catalyzed

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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.

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铜(I)催化丙炔酸、仲胺、醛和甲醛一锅法交叉偶联构建非对称1,4-二氨基丁炔

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

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