Copper(II)-phenanthroline hybrid material as efficient catalyst for the multicomponent synthesis of 1,2,3-triazoles via sequential azide formation/1,3-dipolar cycloaddition

Nunes, Andreia; Djakovitch, Laurent; Khrouz, Lhoussain; Felpin, François‐Xavier; Dufaud, Véronique

doi:10.1016/j.molcata.2016.11.017

Cited by 22 publications

(10 citation statements)

References 39 publications

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“…Initially, imidazole (28) was immobilized on the silica nanomaterial 27 by a nucleophilic attack of 28 on the iodopropylated silica nanomaterial 27 in acetonitrile under reflux for 48 h. The obtained 1-propylimidazole-nanosilica compound ImP-nSiO 2 (29) was filtered, washed with acetonitrile, and dried. The catalyst 29 was treated with pentaerythri-tol tetrabromide (PETB, 30) using NaI in anhydrous toluene under reflux for 24 h. The obtained composite PETB-ImP-nSiO 2 (31) was filtrated, washed with anhydrous toluene, and dried. Then, 28, 31, and NaI were added to acetonitrile, and this was stirred under reflux for 48 h. The obtained nanomaterial G 1 -nSiO 2 (32) was filtrated, washed with acetonitrile, and dried.…”

Section: Reviewmentioning

confidence: 99%

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A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

Shiri¹,

Aboonajmi²

2020

Beilstein J. Org. Chem.

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In recent years, many inorganic silica/carbon-based and magnetic materials have been selected to arrest copper ions through a widespread range of anchoring and embedding methodologies. These inorganic supported nanocatalysts have been found to be efficient, environmentally friendly, recyclable, and durable. In addition, one of the vital issues for expanding new, stable, and reusable catalysts is the discovery of unique catalysts. The basis and foundation of this review article is to consider the recently published developments (2014–2019) in the synthesis and catalytic applications of copper supported by silica nanocomposites, carbon nanocomposites, and magnetic nanocomposites for expanding the “click” chemistry.

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Section: Reviewmentioning

confidence: 99%

“…Further, Dufauda et al reported a copper(II)-phenanthroline complex supported on the SBA-15 architecture, Cu(II)phen@SBA-15 (58) [31]. The preparation is outlined in Scheme 9: Initially, phen-functionalized mesoporous SBA-15 silica (phen@SBA-15, 57) was prepared via dissolving pluronic P123 in acidic water at 35 °C.…”

Section: Reviewmentioning

confidence: 99%

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

Shiri¹,

Aboonajmi²

2020

Beilstein J. Org. Chem.

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“…However, recent publications have described the use of Cu(II) complexes as catalysts without the use of reducing agents. [113][114][115][116][117][118][119][120] Bagherzadeh et al 121 reported in 2019 the preparation of two Cu(II) complexes (Figure 6) and studied their catalytic potentials against the CuAAC reaction in the absence of reducing agents. The authors were able to prepare different 1H-1,2,3-triazole derivatives from a multicomponent reaction between benzyl chloride, sodium azide and different terminal alkynes with good yields.…”

Section: Main Sources Of Cu (Ii) Used In Cuaac Reactionsmentioning

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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“…Nevertheless, these systems are usually homogeneous and suffer from inherent drawbacks: difficulty in separating the catalyst and product, environmental concern, and recyclability. Recent research in this area has focused on beneficial heterogeneous catalysis which can address these problems and has several advantages such as easier separation of catalyst and product(s), better recovery, allowing for reuse of the catalyst systems, and reduced metal contamination in the final products . In this context, magnetic nanoparticles (MNPs) are considered promising catalysts because of their response to an external magnetic field and are thus extensively used in a variety of important organic reactions .…”

Section: Introductionmentioning

confidence: 99%

Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles

Khalili

Rezaee

2019

Applied Organom Chemis

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Magnetic CuFe 2 O 4 /g-C 3 N 4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X-ray diffraction, highresolution transmission electron microscopy, field emission scanning electron microscopy, Fourier infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, and N 2 adsorption-desorption analysis (Brunauer-Emmett-Teller surface area). The utilization of magnetic CuFe 2 O 4 /g-C 3 N 4 enabled superior performance in the one-pot azide-alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any additional agents. The present system is broad in scope and especially practical for the synthesis of macrocyclic triazoles and also tetrazoles. In addition, the catalytic system highly fulfills the demands of "green click chemistry" with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple workup and isolation procedure.

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Copper(II)-phenanthroline hybrid material as efficient catalyst for the multicomponent synthesis of 1,2,3-triazoles via sequential azide formation/1,3-dipolar cycloaddition

Cited by 22 publications

References 39 publications

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

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

Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand‐free click synthesis of diverse 1,2,3‐triazoles and tetrazoles

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