Cu(II)-anchored functionalized mesoporous SBA-15: An efficient and recyclable catalyst for the one-pot Click reaction in water

Roy, Susmita; Chatterjee, Tanmay; Pramanik, Malay; Roy, Anupam Singha; Bhaumik, Asim; Islam, Sk. Manirul

doi:10.1016/j.molcata.2014.01.027

Cited by 66 publications

(41 citation statements)

References 68 publications

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“…If we compare our materials with others catalysts, the assynthesized Si-MCM-41 catalyst seems to be the best for the reactions of cycloaddition [29,45]. In fact, not only the reaction time is decreased (around 15 min), but also the Si-MCM-41 is used as synthesized thus no further preparation is needed.…”

Section: Cycloaddition Reaction Using Si- Ga-or Al-mcm-41 Catalystsmentioning

confidence: 95%

“…Good results were obtained under these conditions from 4-nitrophenyl azide (1) and all the activated alkenes 2 using Et 3 N/calcined mesoporous material Si-MCM-41 (Table 3, entries 21-25). By using Et 3 N/calcined Ga-or Al-MCM-41 (Table 3, entries 1-5 and 11-15), Et 3 N/as-synthetized Si-MCM-41 (Table 3, entries [26][27][28][29][30] and Et 3 N/as-synthetized Ga-or Al-MCM-41 (Table 3, entries 6-10 and 16-20), good yields were still observed using acetylacetone (2a), methyl acetoacetate (2b) and malonodinitrile (2e). However, when using ethyl acetoacetate (2c) and ␣-benzoylacetophenone (2d), moderate yields were noted.…”

Section: Catalytic Experimentsmentioning

confidence: 99%

“…Generally the catalysts for the cycloaddition of azide are solids which contain copper [29,[45][46][47], to our best knowledge, mesoporous Si-Ga-or Al-MCM-41 have never been studied for cycloaddition of aryl azides. Thus the aim of the present research is to compare the catalytic properties of a series of mesoporous catalyst including: (1) Si-MCM-41, (2) Ga-MCM-41, (3) Al-MCM-41, (4) and a mixture between homogeneous/heterogeneous catalysts.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide

Boukoussa

Zeghada

Ababsa

et al. 2015

Applied Catalysis A: General

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International audienceSi-MCM-41, Ga-MCM-41 and Al-MCM-41 mesoporous catalysts (with Si/Al = 80 and Si/Ga = 80) were prepared by direct synthesis under hydrothermal crystallization method using sodium aluminate or gallium sulfate and tetraethyl orthosilicate (TEOS) as aluminum or gallium and silica sources, respectively. The structural features of the materials were determined by various physico-chemical techniques such as X-ray diffraction (XRD), nitrogen sorption at 77 K, Fourier transform infrared spectroscopy (FTIR), scanning and transmission electronic microscopy (SEM, TEM) and thermogravimetric analysis ATG. The catalytic activity of the calcined and as-synthesized catalyst was evaluated through the cycloaddition reaction of 4-nitrophenyl azide with activated alkenes at room temperature under liquid-phase conditions. High yields of 1,2,3-triazole were obtained. For comparison purpose, mixtures of homogeneous and heterogeneous catalyst Et3N/M-MCM-41 (M = Al or Ga) are also tested. The catalyst was used in five consecutive experiments without important loss of activity, confirming its stability. Finally, a new method for preparing triazoles in short reaction times was developed

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Section: Cycloaddition Reaction Using Si- Ga-or Al-mcm-41 Catalystsmentioning

confidence: 95%

Section: Catalytic Experimentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide

Boukoussa

Zeghada

Ababsa

et al. 2015

Applied Catalysis A: General

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“…77 The mesoporous silica SBA-15 was first amine functionalized using 3-amino propyltriethoxysilane (3-APTES) which was then subjected to undergo Schiff base condensation reaction with 2-pyridinecarboxaldehyde to form a new imine functionalized mesoporous SBA-15, followed by grafting of copper acetate onto it, to form Cu@PyIm-SBA-15 material. The catalyst was recycled for five cycles without any significant loss of catalytic activity.…”

Section: Scheme 15mentioning

confidence: 99%

Recent developments in copper nanoparticle-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Lal¹,

Rani²

2016

Arkivoc

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The Cu(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and organic azides generating 1,4-disubstituted 1,2,3-triazoles has attracted considerable attention owing to its consistency, specificity, and biocompatibility. Copper nanoparticles supported on various supports such as agarose, cellulose, chitosan, charcoal, activated carbon, silica gel, aminoclay, polymer support like poly(styrene-co-maleimide) (SMI) and polyvinylpyrrolidone (PVP) have been utilized as heterogeneous catalyst for the synthesis of 1,2,3-triazoles. This review summarizes various straightforward and efficient methods for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles utilizing supported copper nanoparticles as a source of the heterogeneous catalytic species and water as solvent.

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“…Copper-based catalysts can perform the cycloaddition reaction of azides with terminal alkynes by Cu(I) and/or Cu(II) species. [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] Moreover, the performance of Ru-based catalysts on the cycloaddition of azides and terminal alkynes (RuAAC) for the regioselective synthesis of 1,2,3-triazoles has been reported. 26 Particularly, application of nano-metal oxides as catalysts in organic synthesis has been improved because of their significant characteristics.…”

Section: Introductionmentioning

confidence: 99%

Regioselective synthesis of 1,2,3-triazoles catalyzed over ZnO supported copper oxide nanocatalyst as a new and efficient recyclable catalyst in water

Albadi

Alihosseinzadeh²,

Mansournezhad³

2015

ACSi

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The CuO/ZnO nanocatalysts are reported as efficient and recyclable catalysts for the regioselective synthesis of 1,2,3-triazoles from benzyl halides and terminal alkynes in water. The catalysts are synthesized by a co-precipitation method and characterized by BET surface area, XRD, SEM, TEM and EDS analysis. The effect of CuO loading, catalyst amount and solvent was investigated. The catalyst can be recovered by a simple filtration and applied in consecutive runs with no loss of activity.

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Cu(II)-anchored functionalized mesoporous SBA-15: An efficient and recyclable catalyst for the one-pot Click reaction in water

Cited by 66 publications

References 68 publications

Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide

Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide

Recent developments in copper nanoparticle-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles in water

Regioselective synthesis of 1,2,3-triazoles catalyzed over ZnO supported copper oxide nanocatalyst as a new and efficient recyclable catalyst in water

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