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

Research School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

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 language	English
Pages (from-to)	978-985
Number of pages	8
Journal	Organic Chemistry Frontiers
Volume	4
Issue number	6
DOIs	https://doi.org/10.1039/c6qo00787b
Publication status	Published - 1 Jun 2017

ASJC Scopus subject areas

Organic Chemistry

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10.1039/c6qo00787b

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Regioselective Zn(OAc)₂-catalyzed azide-alkyne cycloaddition in water : The green click-chemistry. / Morozova, Maria A.; Yusubov, Mekhman S.; Kratochvil, Bohumil; Eigner, Václav; Bondarev, Alexander A.; Yoshimura, Akira; Saito, Akio; Zhdankin, Viktor V.; Trusova, Marina E.; Postnikov, Pavel S.

In: Organic Chemistry Frontiers, Vol. 4, No. 6, 01.06.2017, p. 978-985.

Research output: Contribution to journal › Article › peer-review

Morozova, Maria A. ; Yusubov, Mekhman S. ; Kratochvil, Bohumil ; Eigner, Václav ; Bondarev, Alexander A. ; Yoshimura, Akira ; Saito, Akio ; Zhdankin, Viktor V. ; Trusova, Marina E. ; Postnikov, Pavel S. / Regioselective Zn(OAc)₂-catalyzed azide-alkyne cycloaddition in water : The green click-chemistry. In: Organic Chemistry Frontiers. 2017 ; Vol. 4, No. 6. pp. 978-985.

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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.",

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