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

Maria A. Morozova, Mekhman S. Yusubov, Bohumil Kratochvil, Václav Eigner, Alexander A. Bondarev, Akira Yoshimura, Akio Saito, Viktor V. Zhdankin, Marina E. Trusova, Pavel S. Postnikov

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14 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)978-985
Number of pages8
JournalOrganic Chemistry Frontiers
Volume4
Issue number6
DOIs
StatePublished - Jun 2017

Bibliographical note

Funding Information:
This work was supported by the Russian Ministry of Education and Science (Scientific Program no. 4.5924.2017). The authors greatly acknowledge the Laboratory of Physical-Chemical Analytical Methods of Tomsk State University for the NMR and HRMS analyses.

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