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

Морозова, М. А.; Yusubov, Mekhman S.; Kratochvíl, Bohumil; Eigner, Václav; Bondarev, Alexander A.; Yoshimura, Atsushi; Saitô, Akio; Zhdankin, Viktor V.; Trusova, Marina E.; Postnikov, Pavel

doi:10.1039/c6qo00787b

Cited by 50 publications

(23 citation statements)

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“…In 2014, Trusova and coworkers developed the Zn(OAc) 2 -based catalytic system for AAC reactions in water, which could be applied to synthesize trisubstituted triazoles 80 from internal alkynes (Scheme 39b). [58] This strategy shows good tolerance towards diverse symmetrical internal alkynes (80 a & 80 b for instance). Exclusive regioselectivities were observed in the treatments of unsymmetrical internal alkynes bearing a bulky silyl group (80 c).…”

Section: Zna I Acmentioning

confidence: 99%

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Ding

2020

Asian J Org Chem

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Metal-catalyzed azide-alkyne cycloaddition reactions represent the most convenient and atom-economic way to construct robust 1,2,3-triazole units. Remarkable copperand ruthenium-based catalytic systems have been well established for regioselective preparation of 1,4-and 1,5disubstituted 1,2,3-triazoles, both of which have been widely utilized in various areas. In comparison, exploitation of efficient methods to promote the cycloaddition of azides with internal alkynes to afford 1,4,5-trisubstituted 1,2,3triazole motifs with high regioselectivity is still challenging and attractive. This review provides a thorough summary of the developments in metal-catalyzed cycloaddition of azides with internal alkynes. Besides discussions about mechanism and scope, applications of these strategies were also briefly overviewed.

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Section: Zna I Acmentioning

confidence: 99%

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Ding

2020

Asian J Org Chem

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“…An interesting Zn(OAc) 2 -catalyzed azide-alkyne cycloaddition was developed by Postnikov and his research group affording 1,4-disubstituted 1,2,3-triazoles [20].…”

Section: Metal-catalyzed 13-dipolar Cycloadditionmentioning

confidence: 99%

1,2,3-Triazoles: Synthesis and Biological Application

Ali¹

2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Among nitrogen-containing heterocyclic compounds, 1,2,3-triazoles are privileged structure motif and received a great deal of attention in academics and industry. Even though absent in nature, 1,2,3-triazoles have found broad applications in drug discovery, organic synthesis, polymer chemistry, supramolecular chemistry, bioconjugation, chemical biology, fluorescent imaging, and materials science. Therefore, the development of facile and straightforward methodology for the synthesis of 1,2,3-triazoles is of noteworthy interest. In this study, emphasis will be given to numerous synthetic approaches for the synthesis of 1,2,3-triazoles, especially the popular click chemistry approach. Furthermore, several biological activities of this promising heterocycle will also be discussed.

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“…[7][8][9][10] Moreover, the use of Cu(II) species often requires a reducing agent making the process less atom-economic. Other transition metals like Ru, Rh, Ag, Au, Ir and Zn have also been used as catalysts in AAC, [10][11][12] though their efficacy is limited in terms of regioselectivity of the product, general applicability, use of precious metals/ligands and tricky procedure for making the catalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Ni–rGO–zeolite nanocomposite: an efficient heterogeneous catalyst for one-pot synthesis of triazoles in water

Choudhury

Chattopadhyay

et al. 2021

Mater. Adv.

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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.

Cited by 50 publications

References 54 publications

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

1,2,3-Triazoles: Synthesis and Biological Application

Ni–rGO–zeolite nanocomposite: an efficient heterogeneous catalyst for one-pot synthesis of triazoles in water

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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.

Cited by 50 publications

References 54 publications

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

1,2,3-Triazoles: Synthesis and Biological Application

Ni–rGO–zeolite nanocomposite: an efficient heterogeneous catalyst for one-pot synthesis of triazoles in water

Contact Info

Product

Resources

About

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