Controlling chemoselectivity in copper-catalyzed decarboxylative A3/A3 cross-couplings: direct formation of unsymmetrical 1,4-diamino-2-butynes

Panfeng Zhao; Huangdi Feng; Haoran Pan; Zhihua Sun; Minchao Tong

doi:10.1039/C6QO00499G

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Controlling chemoselectivity in copper-catalyzed decarboxylative A³/A³ cross-couplings: direct formation of unsymmetrical 1,4-diamino-2-butynes†

Panfeng Zhao,^a Huangdi Feng,*^a Haoran Pan,^a Zhihua Sun^a and Minchao Tong*^b

Author affiliations

* Corresponding authors

^a College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, China
E-mail: hdfeng@sues.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China
E-mail: minchaotong@sioc.ac.cn

Abstract

A direct cross-coupling of propiolic acid with two kinds of in situ formed iminiums has been achieved via the CuI/CuCl₂-catalyzed decarboxylative A³/A³ domino process. This novel protocol to synthesise unsymmetrical 1,4-diamino-2-butynes is operationally simple in an atom- and step-economical manner, and provides products in moderate to excellent yields with high chemoselectivity.

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Article information

DOI: https://doi.org/10.1039/C6QO00499G
Article type: Research Article
Submitted: 29 Aug 2016
Accepted: 09 Oct 2016
First published: 10 Oct 2016

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Org. Chem. Front., 2017,4, 37-41

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Controlling chemoselectivity in copper-catalyzed decarboxylative A³/A³ cross-couplings: direct formation of unsymmetrical 1,4-diamino-2-butynes

P. Zhao, H. Feng, H. Pan, Z. Sun and M. Tong, Org. Chem. Front., 2017, 4, 37 DOI: 10.1039/C6QO00499G

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