Issue 6, 2017
From the journal:

Organic Chemistry Frontiers

Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry†

Maria A. Morozova,a   Mekhman S. Yusubov,b   Bohumil Kratochvil,cd   Václav Eigner,d   Alexander A. Bondarev,e   Akira Yoshimura,bf   Akio Saito, ORCID logo g   Viktor V. Zhdankin,bf   Marina E. Trusova*a  and  Pavel S. Postnikov ORCID logo *b  

* Corresponding authors

a Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 43 Lenin ave., 634050 Tomsk, Russia
E-mail: trusova@tpu.ru
Tel: +7(3822)563-861

b Department of Technology of Organic Substances and Polymer Materials, National Research Tomsk Polytechnic University, 43 Lenin ave., 634050 Tomsk, Russia
E-mail: postnikov@tpu.ru
Tel: +79039136029

c Department of Physical and Analytical Chemistry, National Research Tomsk Polytechnic University, 43 Lenin ave., 634050 Tomsk, Russia

d Department of Solid State Chemistry, University of Chemistry and Technology, Prague, Technicka 5, Czech Republic

e Department of Biomedicine, Altai State University, Barnaul, Lenina av. 61, Russia

f Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA

g Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology Koganei, Tokyo 184-8588, Japan

Abstract

A new method of azide–alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.

Graphical abstract: Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry

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Article information

DOI
https://doi.org/10.1039/C6QO00787B
Article type
Research Article
Submitted
06 Dec 2016
Accepted
08 Feb 2017
First published
08 Feb 2017
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2017,4, 978-985

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Regioselective Zn(OAc)2-catalyzed azide–alkyne cycloaddition in water: the green click-chemistry

M. A. Morozova, M. S. Yusubov, B. Kratochvil, V. Eigner, A. A. Bondarev, A. Yoshimura, A. Saito, V. V. Zhdankin, M. E. Trusova and P. S. Postnikov, Org. Chem. Front., 2017, 4, 978 DOI: 10.1039/C6QO00787B

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