Microwave-Assisted Cu(I)-Catalyzed Synthesis of Unsymmetrical 1,4-Diamino-2-butynes via Cross-A3-Coupling/Decarboxylative A3-Coupling

Xianjun Xu; Huangdi Feng; Erik V Van der Eycken

doi:10.1021/acs.joc.1c00537

Microwave-Assisted Cu(I)-Catalyzed Synthesis of Unsymmetrical 1,4-Diamino-2-butynes via Cross-A³-Coupling/Decarboxylative A³-Coupling

J Org Chem. 2021 Oct 15;86(20):14036-14043. doi: 10.1021/acs.joc.1c00537. Epub 2021 Apr 23.

Authors

Xianjun Xu¹, Huangdi Feng², Erik V Van der Eycken^{1

3}

Affiliations

¹ Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven 3001, Belgium.
² College of Chemistry and Chemical Engineering & Shanghai Engineering Research Center of Textile Chemistry and Cleaner Production, Shanghai University of Engineering Science, Shanghai 201620, China.
³ Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russia.

PMID: 33890472
DOI: 10.1021/acs.joc.1c00537

Abstract

1,4-Diamino-2-butynes display both chemical and physiological properties. Here a highly efficient synthesis avenue to generate unsymmetric 1,4-diamino-2-butynes has been developed by microwave-assisted Cu(I)-catalyzed cross-A³-coupling/decarboxylative coupling of two different amines, formaldehyde, and propiolic acid through a domino process. This multicomponent reaction provides a series of target products in moderate to good yields with high chemoselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines
Catalysis
Diamines*
Microwaves*

Substances

Amines
Diamines
1,4-diamino-2-butyne