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


刘博瑜, 徐仙君, 黄立梁, 冯煌迪   

  1. 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;
  • 基金资助:

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   

  1. 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).

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