Copper iodide nanoparticles on poly(4-vinyl pyridine): A new and efficient catalyst for multicomponent click synthesis of 1,4-disubstituted-1,2,3-triazoles in water

Albadi, Jalal; Keshavarz, Mosadegh; Shirini, Farhad; Vafaie-nezhad, Masoumeh

doi:10.1016/j.catcom.2012.05.023

Cited by 76 publications

(35 citation statements)

References 19 publications

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“…These results showed that the nature of substitution did not have a significant impact on the outcome of the reaction. It was found that cyclization of the dibenzyl chloride with phenyl acetylene provided bistriazole in high yield ( Moreover, this protocol worked well in the case of more complex structures containing coumarin, isatin, and steroid groups and provided the corresponding 1,4-triazoles in good yield ( Table 2, entry [23][24][25][26][27][28]. It is also interesting to note that in all tested examples in this protocol, only 1,4-disubstituted triazoles were obtained.…”

Section: Entrymentioning

confidence: 64%

Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe$_{3}$O$_{4}$ MNPs in a water/PEG$_{300}$ system

Hassanpour¹,

Maleki²,

Hosseini³

et al. 2017

Turk J Chem

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Abstract:A highly dispersible and magnetically recoverable Cu-PEI@Fe 3 O 4 MNPs catalyst was prepared and successfully applied in one-pot three-component coupling of terminal alkynes, sodium azide, and alkyl bromides/chlorides in water to give 1,4-disubstituted 1,2,3-triazoles with good to excellent yields. The catalyst was fully characterized with FT-IR, TGA, TEM, SEM, VSM, EDX, cyclic voltammetry, and ICP-AES spectroscopic techniques. Furthermore, the catalyst was easily recycled by an external magnet and successfully reused six times in the reaction without significant loss of its catalytic activity and copper leaching. The large-scale reaction was also carried out in the absence of any base and reducing agent even with 0.1 mol% of the catalyst in aqueous media, making this protocol a good candidate for practical applications.

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Section: Entrymentioning

confidence: 64%

Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe$_{3}$O$_{4}$ MNPs in a water/PEG$_{300}$ system

Hassanpour¹,

Maleki²,

Hosseini³

et al. 2017

Turk J Chem

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“…Recently, heterogeneous copper(I) catalysts based on silica (Miao and Wang 2008; Shamim and Paul 2010), montmorillonite (Jlalia et al 2008), zeolites (Bénéteau et al 2010; Chassaing 2010) and Cu in charcoal (Sharghi et al 2009) and Cu nanoporous skeleton catalyst (Jin et al 2011, 2012; Asao et al 2012) have been developed. There are also some reports on using polymer supported CuI as recoverable catalyst for this cyclization (Albadi et al 2012a, 2012b; Albadi and Keshavarz 2013; Girard et al 2006; Jlalia et al 2010; Dervaux and Du Prez 2012). …”

Section: Introductionmentioning

confidence: 99%

Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides

et al. 2013

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Macroporous polymer supported nanoparticles of copper(I) iodide catalyst and macroporous polymer supported azide reagent were used to simplify the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from various benzyl halides following the green chemistry principles. This new one-pot protocol facilitates the workup of the reaction and provides the products in short times and at high yields. Heterogeneous catalyst and reagent can be reloaded and reused at least for 5 runs without significant decrease in the yields.Electronic supplementary materialThe online version of this article (doi:10.1186/2193-1801-2-64) contains supplementary material, which is available to authorized users.

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“…25 Recently, we have reported the preparation of copper iodide nanoparticles supported on poly(4-vinylpyridine) (P 4 VPy-CuI) and their application for the click synthesis of triazole derivatives. [26][27] In continuation of these studies, we now report the application of this reagent to the chemoselective synthesis of pentaerythritol diacetals from aromatic aldehydes under solvent-free conditions (Scheme 1).…”

mentioning

confidence: 96%

A Green Recyclable Poly(4-Vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst for the Chemoselective Synthesis of Pentaerythritol Diacetals from Aromatic Aldehydes

Albadi¹,

Iravani

Shirini

et al. 2012

Journal of Chemical Research

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Poly(4-vinylpyridine)-supported copper(I) iodide nanoparticles have been used as an efficient, green recyclable catalyst for the chemoselective synthesis of pentaerythritol diacetals from aromatic aldehydes and pentaerythritol under solvent-free conditions. This catalyst was reused six times without any loss of its activity.We thank the Behbahan Khatam Alanbia University of Technology for partial support of this work.

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Copper iodide nanoparticles on poly(4-vinyl pyridine): A new and efficient catalyst for multicomponent click synthesis of 1,4-disubstituted-1,2,3-triazoles in water

Cited by 76 publications

References 19 publications

Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe$_{3}$O$_{4}$ MNPs in a water/PEG$_{300}$ system

Efficient multicomponent synthesis of 1,2,3-triazoles catalyzed by Cu(II) supported on PEI@Fe$_{3}$O$_{4}$ MNPs in a water/PEG$_{300}$ system

Macroporous polymer supported azide and nanocopper (I): efficient and reusable reagent and catalyst for multicomponent click synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from benzyl halides

A Green Recyclable Poly(4-Vinylpyridine)-Supported Copper Iodide Nanoparticle Catalyst for the Chemoselective Synthesis of Pentaerythritol Diacetals from Aromatic Aldehydes

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