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 output: Contribution to journalArticle

7 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 languageEnglish
Pages (from-to)978-985
Number of pages8
JournalOrganic Chemistry Frontiers
Volume4
Issue number6
DOIs
Publication statusPublished - 1 Jun 2017

Fingerprint

Alkynes
Azides
Cycloaddition
Triazoles
Water
Nuclear magnetic resonance
Catalysts

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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 journalArticle

@article{cef946c984e44e938db218e017ba1d47,
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.}",
year = "2017",
month = "6",
day = "1",
doi = "10.1039/c6qo00787b",
language = "English",
volume = "4",
pages = "978--985",
journal = "Organic Chemistry Frontiers",
issn = "2052-4110",
publisher = "Royal Society of Chemistry",
number = "6",

}

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.

PY - 2017/6/1

Y1 - 2017/6/1

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.

UR - http://www.scopus.com/inward/record.url?scp=85021737763&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85021737763&partnerID=8YFLogxK

U2 - 10.1039/c6qo00787b

DO - 10.1039/c6qo00787b

M3 - Article

VL - 4

SP - 978

EP - 985

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

SN - 2052-4110

IS - 6

ER -