Cellulose supported cuprous iodide nanoparticles (Cell-CuI NPs): a new heterogeneous and recyclable catalyst for the one pot synthesis of 1,4-disubstituted – 1,2,3-triazoles in water

Chavan, Pramod V.; Pandit, Kapil S.; Desai, Uday V.; Kulkarni, Makarand A.; Wadgaonkar, Prakash P.

doi:10.1039/c4ra05080k

Cited by 91 publications

(38 citation statements)

References 81 publications

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“…It is worth mentioning that the results showed alkyl and aryl halides react better than haloketones in terms of yields and reaction times. The efficiency of CuI@[PMMA‐co‐MI] in click reaction was also compared with that of previously reported catalysts under various reaction conditions (Table ) . By comparison, it can be concluded that CuI@[PMMA‐co‐MI] as a novel nanocatalyst has several merits such as higher or comparable yield of the desired product in shorter reaction time.…”

Section: Resultsmentioning

confidence: 95%

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

Pourmohammad

Heravi

Ahmadi

et al. 2019

Applied Organom Chemis

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A CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] (CuI@[PMMA‐co‐MI]) nanocatalyst was prepared from in situ polymerization and functionalization of poly[(methyl methacrylate)‐co‐(maleic anhydride)] and well characterized using various techniques. From a computational viewpoint, we assessed two complexation models between copper nanoparticles and [PMMA‐co‐MI]. In this line, the metal–ligand interaction strength was also studied via density functional theory calculations and frontier molecular orbital analysis. Moreover, for presenting a quantitative description of the electronic features of immobilization of copper nanoparticles on polymeric support, the topological analysis of electron density and its Laplacian was performed through quantum theory of atoms in molecules. Finally, the catalytic activity of CuI@[PMMA‐co‐MI] as a heterogeneous nanocatalyst was successfully examined in the highly regioselective synthesis of 1,4‐disubstituted 1,2,3‐triazoles via click reaction.

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Section: Resultsmentioning

confidence: 95%

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

Pourmohammad

Heravi

Ahmadi

et al. 2019

Applied Organom Chemis

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“…Likewise, peaks at δ 76.74 and 75.42 ppm in 13 C‐NMR spectrum of 2 , were attributed to acetylene carbon atoms. The reaction of aryl/benzyl azide with alkyne ( 2 ) was tested under various reaction conditions, wherein the formation of corresponding triazole 3 and 5 (Scheme ) found better with Cell‐CuI‐NPs as heterogeneous catalyst by heating the reaction mixture at 70 °C in aqueous condition with high yield and less time as compare to other catalyst systems like‐CuI/DIPEA and CuSO 4 .5H 2 O/sodium ascorbate as shown in Table …”

Section: Introductionmentioning

confidence: 99%

Cellulose‐Supported CuI‐Nanoparticles‐Mediated Green Synthesis of Trifluoromethylbenzoate‐Linked Triazoles for Pharmacological & DFT study

et al. 2019

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A green heterogeneous catalyst cellulose‐supported CuI‐nanoparticles employed for efficient synthesis of 4‐trifluoromethylbenzoate‐linked triazole in high yield from 4‐trifluoromethyl‐benzoic acid prop‐2‐ynyl ester and aryl/benzyl azide under aqueous condition. All triazoles were successfully characterized by IR, 1H‐NMR, 13C‐NMR, HRMS and finally supported by X‐ray crystallographic structure of 4‐trifluoromethyl‐benzoic acid 1‐phenyl‐1H‐[1,2,3]triazol‐4‐ylmethyl ester. Antibacterial study revealed that triazoles substituted by 4‐NO2 and 4‐Cl group to the benzyl and benzene ring displayed good to comparable activity as compare to commonly used drug ciprofloxacin. Likewise, triazoles substituted with a 4‐NO2 group on benzyl ring, unsubstituted aryl and 4‐F substituted aryl showed better antifungal activity when compared with commonly used antifungal drug fluconazole. Further, the computational study by DFT (B3PW91) level with 6–311G(d,p) basis set studied chemical reactivities, chemical hardness and molecular stability of triazole by frontier molecular orbital and molecular electrostatic potential study. The DFT results were in good agreement with pharmacological studies.

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“…From the synthetic point of view the reaction has witnessed two important developments; (i) replacement of homogeneous catalysts by heterogeneous‐reusable catalysts and, (ii) in situ generation of azides . As far as use of heterogeneous catalysts is concerned, in the recent years copper salts as well as copper nanoparticles on various supports and in different oxidation states have been demonstrated as efficient catalysts in the synthesis of 1,2,3‐triazoles . On the other hand, as far as in situ generation of azides is concerned organic halides, epoxides, as well as arylboronic acids have been widely used as azide precursors .…”

Section: Introductionmentioning

confidence: 99%

Bentonite ‐ Clay ‐ Supported Cuprous Iodide Nanoparticles (BENT‐ CuI NPs): A New Heterogeneous Catalyst in Diversity ‐ Oriented Synthesis of 1, 2, 3‐ Triazoles in Aqueous Medium

et al. 2019

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Bentonite clay supported cuprous iodide nanoparticles (BENT‐CuI NPs) were prepared and demonstrated for the first time as an efficient heterogeneous catalyst in diversity oriented, green synthesis of 1,2,3‐triazoles by one‐pot, three component reaction between alkyl halides, arylboronic acids, or epoxides with alkynes and sodium azide in aqueous medium. The catalyst was characterized by Inductively Coupled Plasma Atomic Emission Spectroscopy (ICP‐AES), Energy Dispersive X‐ray Spectroscopy(EDS), Scanning Electron Microscopy (SEM), X‐Ray Powder Diffraction (XRD), Transmission Electron Microscopy (TEM) as well as Brunauer‐Emmett‐Teller (BET) techniques and was found to be reusable for five consecutive runs without significant loss of activity.

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Cellulose supported cuprous iodide nanoparticles (Cell-CuI NPs): a new heterogeneous and recyclable catalyst for the one pot synthesis of 1,4-disubstituted – 1,2,3-triazoles in water

Cited by 91 publications

References 81 publications

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

In situpreparation and characterization of novel CuI‐functionalized poly[(methyl methacrylate)‐co‐maleimide] as an efficient heterogeneous catalyst in the regioselective synthesis of 1,2,3‐triazoles via click reaction: Experimental and computational chemistry

Cellulose‐Supported CuI‐Nanoparticles‐Mediated Green Synthesis of Trifluoromethylbenzoate‐Linked Triazoles for Pharmacological & DFT study

Bentonite ‐ Clay ‐ Supported Cuprous Iodide Nanoparticles (BENT‐ CuI NPs): A New Heterogeneous Catalyst in Diversity ‐ Oriented Synthesis of 1, 2, 3‐ Triazoles in Aqueous Medium

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