AgN(CN)2/DIPEA/H2O-EG: a highly efficient catalytic system for synthesis of 1,4-disubstituted-1,2,3 triazoles at room temperature

Ali, Abdul Aziz; Chetia, Mitali; Saikia, Bishwajit; Saikia, Prakash J.; Sarma, Diganta

doi:10.1016/j.tetlet.2015.09.025

Cited by 52 publications

(21 citation statements)

References 52 publications

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“…One should recall here that the uncatalyzed Huisgen reaction that yields such mixtures of isomeric cycloadducts works under ambient or mild conditions when substrates possess electron-withdrawing groups [25]. Sarma's group then compared various silver sources in AAC reactions conducted in H 2 O/ethylene glycol (EG) under ambient conditions without exclusion of air [98]. The ligands and solvents played a critical role in their approach.…”

Section: The Agaac Reactionsmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

279

162

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Highlights-The review is focused on the mechanistic aspects and recent trends (since 2012) of the metal-catalyzed azide-alkyne cycloaddition (MAAC) so-called "click" reactions with catalysts based on various metals (Cu, Ru, Ag, Au, Ir, Ni, Zn, Ln), although Cu (I) catalysts are still the most used ones.-These MAAC reactions are by far the most common click reactions relevant to the "green chemistry" concept.-Mechanistic investigations are essential to reaction improvements and subsequent applications, and indeed as shown in this review the proposed mechanisms have been multiple during the last decade based on theoretical computations and experimental search of intermediates.-New trends are also presented here often representing both exciting approaches for various applications and new challenges for further mechanistic investigations.

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Section: The Agaac Reactionsmentioning

confidence: 99%

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Changlong

Ikhlef

Kahlal

et al. 2016

Coordination Chemistry Reviews

279

162

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“…First report of the use of ruthenium in the preparation of 1H-1,2,3-triazole derivatives. 278 The use of metals such as silver, [282][283][284][285][286] gold, 287,288 iridium, 289,290 nickel, 291 zinc, 292,293 samarium 294 and lanthanum 295 have also been reported. Further details as well as the mechanistic aspects involved in the use of these different metals can be found in the review by Wang et al 296 and in the recent work of Gomes et al 35 Recently, Zheng's research group reported the use of Di-µ-chloro-tetracarbonyldirhodium(I), a rhodium(I) complex, in the catalysis of the reaction between internal alkynes and azides in a highly regioselective form.…”

Section: Use Of Other Transition Metals In Cycloaddition Reactions Involving Azides and Alkynes (Maac)mentioning

confidence: 99%

1,2,3- Triazoles: general and key synthetic strategies

Santos¹,

Oliveira²,

Oliveira³

et al. 2020

Arkivoc

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The applications of the 1H-1,2,3-triazole derivatives are particularly attractive and have received prominent attention in scientific research. The characteristics of these heterocycles motivated the development of different strategies for their preparation and molecular diversification. Most of the synthetic procedures available in the literature are based on catalysis with copper salts. Therefore, this review has as complementary central focus and updates the information about the properties and the main methods for the preparation of 1H-1,2,3-triazole derivatives, with emphasis on methods involving 1,3-dipolar cycloaddition between organic azides and terminal alkynes catalyzed by copper.

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“…have also been efficiently manifested for AAC reaction. [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40] Among the 12 principles of Green Chemistry, the use of non-toxic and/or volatile organic solvents, minimal generation of organic wastes, atom-economic synthesis and use of environmentally benign chemicals have introduced an upsurging interest in contemporary organic synthesis. This field also emerging with the use of various nonconventional energy sources such as microwave, ultrasound, mechanical mixing, electrochemical methods and visible light driven organic transformations.…”

Section: Introductionmentioning

confidence: 99%

Cu salts-free mechanochemical approach towards multi-functionalized 1,2,3-triazoles and anti-seizure drug Rufinamide analogs

Bhattacherjee

Коvalev

Kopchuk

et al. 2022

Preprint

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Highly regiospecific, copper salts-free and neat conditions have been demonstrated for the 1,3-dipolar Azide-Alkyne Cycloaddition (AAC) reactions under mechanochemical conditions. A group of structurally challenging alkynes and heterocyclic derivatives was efficiently implemented to achieve highly functionalized 1,4-disubstituted-1,2,3-triazoles in good to excellent yield by using the Cu beads without generation of unwanted byproducts. Furthermore, high-speed ball milling (HSBM) strategy has also been extended to the synthesis of commercially available pharmaceutical agent, Rufinamide, an antiepileptic drug (AED) and its analogues. The same strategy was also applied for the synthesis of Cl-derivative of Rufinamide. Analysis of the single crystal XRD data of the triazole was also performed for the final structural confirmation. The Cu beads can be easily recoverable from the reaction mixture and used for the further reactions without any special treatment.

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AgN(CN)2/DIPEA/H2O-EG: a highly efficient catalytic system for synthesis of 1,4-disubstituted-1,2,3 triazoles at room temperature

Cited by 52 publications

References 52 publications

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

Metal-catalyzed azide-alkyne “click” reactions: Mechanistic overview and recent trends

1,2,3- Triazoles: general and key synthetic strategies

Cu salts-free mechanochemical approach towards multi-functionalized 1,2,3-triazoles and anti-seizure drug Rufinamide analogs

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