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

doi:10.1039/c6qo00787b

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

Chemistry & Biochemistry

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

43 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 language	English (US)
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
State	Published - 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.

Publisher Copyright:
© 2017 the Partner Organisations.

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10.1039/c6qo00787b

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@article{041a424e0d994c94a2958a769177e035,

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

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.",

author = "Morozova, {Maria A.} and Yusubov, {Mekhman S.} and Bohumil Kratochvil and V{\'a}clav Eigner and Bondarev, {Alexander A.} and Akira Yoshimura and Akio Saito and Zhdankin, {Viktor V.} and Trusova, {Marina E.} and Postnikov, {Pavel S.}",

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. Publisher Copyright: {\textcopyright} 2017 the Partner Organisations.",

year = "2017",

month = jun,

doi = "10.1039/c6qo00787b",

language = "English (US)",

volume = "4",

pages = "978--985",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

publisher = "Royal Society of Chemistry",

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}

TY - JOUR

T1 - Regioselective Zn(OAc)2-catalyzed azide-alkyne cycloaddition in water

T2 - The green click-chemistry

AU - Morozova, Maria A.

AU - Yusubov, Mekhman S.

AU - Kratochvil, Bohumil

AU - Eigner, Václav

AU - Bondarev, Alexander A.

AU - Yoshimura, Akira

AU - Saito, Akio

AU - Zhdankin, Viktor V.

AU - Trusova, Marina E.

AU - Postnikov, Pavel S.

N1 - 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. Publisher Copyright: © 2017 the Partner Organisations.

PY - 2017/6

Y1 - 2017/6

N2 - 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.

AB - 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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