Biosynthesis of Fe, Pd, and Fe–Pd bimetallic nanoparticles and their application as recyclable catalysts for [3 + 2] cycloaddition reaction: a comparative approach

Mishra, Kanchan; Basavegowda, Nagaraj; Lee, Yong Rok

doi:10.1039/c5cy00099h

Cited by 71 publications

(43 citation statements)

References 64 publications

(130 reference statements)

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“…The strong band in the region between 800 and 400 cm −1 may be due the stretching vibration of Fe O bonds in IONPs. 37 The S. chinensis leaf extract showed strong bands at 3227, 1555, 1373, and 1016 cm −1 . The broad band at 3227 cm −1 was assigned to the hydrogen bonded O H stretching vibration in the leaf extract, which shifted to 3352 cm −1 in the nanoparticles, confirming the capping by biomolecules.…”

Section: Resultsmentioning

confidence: 95%

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Magnetically Separable Iron Oxide Nanoparticles: An Efficient and Reusable Catalyst for Imino Diels–Alder Reaction

Basavegowda

Mishra

Lee

et al. 2016

Bulletin Korean Chem Soc

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Iron oxide nanoparticles were synthesized using Saururus chinensis (S. chinensis) leaf extract as a reducing and stabilizing agent via ultrasonication. The size, morphology, crystallinity, elemental composition, weight loss, surface chemical state, and magnetic properties of the synthesized nanoparticles were investigated. The synthesized nanoparticles were used as an efficient and recyclable catalyst for the synthesis of a variety of 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives by the imino Diels-Alder reaction. After the reaction, the catalyst was recovered by an external magnetic field. The recovered catalyst was then reused in a subsequent reaction under identical conditions. The recycled iron oxide nanoparticles (IONPs) were reused five times without any significant loss of catalytic activity. Keywords: Iron oxide nanoparticles, Saururus chinensis, Ferromagnetic, Imino Diels-Alder reactionCatalysts are crucial for green chemistry because they allow the development of synthetic steps to the desired products using sustainable resources 1,2 rather than polluting the environment using chemical processes. A vital property of catalysts is their ability to be recovered easily.3 Therefore, metal-nanoparticles are attractive catalysts because of their high selectivity, activity, and harmony with improved reusability. [4][5][6][7] Among the diverse properties of nanoparticles, the size, crystallinity, monodispersity, and elemental composition have a significant effect on the catalytic process. 8,9 Homogenous catalysts usually dissolve in reaction mixture, thus furnish more easily-accessible active catalytic sites, which results in mild reaction conditions and good selectivity. These catalysts, however, have very few usages due to the separating problems in the products contaminated with residuals and recycling is very expensive. The removal of catalysts from the reaction mixture is always demanding by numerous techniques. Over the past few decades, the use of iron-based catalysts in synthetic chemistry has increased rapidly 10 due to it being a relatively nontoxic and inexpensive element. In the general context of nanocatalysis, magnetic nanomaterials, in particular iron oxide nanoparticles, have attracted considerable attention as an inexpensive nanocatalyst that can be separated and recycled. 21 Catalytically active IONPs can be recovered easily from a reaction mixture using an external magnetic field or centrifugation. 22The tetrahydroquinoline moiety present in natural products exhibits a wide range of biological activities. [23][24][25] The imino Diels-Alder reaction between N-arylimines and dienophiles is a facile synthetic approach for the formation of nitrogencontaining heterocyclic compounds, including tetrahydroquinoline derivatives. [26][27][28] Although many methods for the synthesis of 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives have been reported, [29][30][31] there is still a demand for facile, less hazardous, cost efficient, and environmentally friendly catalysts. ...

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Section: Resultsmentioning

confidence: 95%

“…The spectra (Figure ) indicated bioactive molecules containing OH, CO, and CO functional groups present in the plant extract, which acted as a capping agent of synthesized iron oxide nanoparticles. The strong band in the region between 800 and 400 cm −1 may be due the stretching vibration of FeO bonds in IONPs . The S .…”

Section: Resultsmentioning

confidence: 99%

Magnetically Separable Iron Oxide Nanoparticles: An Efficient and Reusable Catalyst for Imino Diels–Alder Reaction

Basavegowda

Mishra

Lee

et al. 2016

Bulletin Korean Chem Soc

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“…Compound 12a was separated easily by column chromatography and its identity confirmed by comparing its spectral data with the literature [29,30]. Under the optimized reaction conditions, additional reactions for the synthesis of various naphtho[1,2-b]furan-3-carboxamides 12b-12q were carried out and afforded in good yields (82-98 %).…”

Section: Synthetic Chemistrymentioning

confidence: 99%

“…Recently, the synthesis of naphtho [1,2-b]furans using In(OTf) 3 and Fe-Pd bimetallic nanoparticlescatalyzed reactions was reported [29,30]. Although a number of methods for the synthesis of these compounds have been reported, there have been few biological evaluations of naphtho [1,2-b]furans [31][32][33][34][35][36].…”

Section: Introductionmentioning

confidence: 98%

$$\hbox {Re}_{2}\hbox {O}_{7}$$ Re 2 O 7 -catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation

2015

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Diverse naphtho[1,2-b]furan-3-carboxamide derivatives 12a-12q were synthesized in high yield via the novel Re2O7-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones with β-ketoamides as the key step. This methodology offers several advantages, such as environmentally benign character, the use of a mild catalyst, high yields, and ease of handling. The synthesized compounds were screened for their tyrosinase inhibitory, antioxidant, and antibacterial activities. The results showed that compound 12c exhibited excellent tyrosinase inhibitory activity with an IC50 of 13.48 μg/mL, which is comparable to that of kojic acid (IC50 = 19.45 μg/mL). Compounds 12a, 12b, and 12i displayed moderate antioxidant activities in a DPPH assay. Compound 12m showed good activity against S. aureus (MIC = 16 μg/mL), and compound 12p was found to be active against E. coli (MIC = 16 μg/mL).

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“…Amidst noble metals, palladium (Pd) has carved a unique niche in the realm of cross‐coupling reactions apart from oxidation and reduction reactions . The dilution of the expensive and scarce Pd by suitable selection of inexpensive first row transition metals for the fabrication of the heteronanostructure seems economical . Along these lines, earth‐abundant metals endowing magnetic credentials apt for 3R approach (recoverable, robust and recyclable) forms a crucial facet of sustainability .…”

Section: Introductionmentioning

confidence: 99%

Sustainable Redox Chemistry Route to Multifaceted Fe‐Pd Heteronanostructure: Delving into the Synergistic Influence in Catalysis

Pramanik

Das

et al. 2017

ChemistrySelect

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The biomimetic concept to decipher the ‘enigma of metalloenzymes’ in integrating two metals in designing a heteronanostructure with multifunctional attributes seems inspiring. In this pursuit, we report a versatile route to Fe−Pd heteronanostructure based on the redox chemistry utilizing the galvanic potentials of the metals, in lieu of an external reducing agent used so far. The synergism between two metal centers has been delved into for multifaceted catalytic applications. The synthesized nanomaterial has been extensively characterized by techniques such as UV‐Vis, FTIR, XRD, SEM‐EDX, HRTEM, BET, VSM, ICP and Mössbauer spectroscopy. The formation of the heteronanostructure with Fe and Pd is clearly evident from HRTEM image and EDS mapping analysis. Mössbauer spectra are consistent with the superparamagnetic nature of the material. Fe−Pd heteronanostructure showed excellent aqueous‐phase catalytic activities for Suzuki coupling reactions with challenging substrates like heteroaryl bromides and aryl chlorides, and reductions of 4‐nitrophenol to 4‐aminophenol and Cr(VI) to Cr(III). Interestingly, in all the three catalytic reactions, Fe−Pd heteronanostructure showed superior activity over its monometallic counterpart substantiating to the cooperative influence of the two metals. Low catalyst loading, shorter reaction times, ‘in water’ reactions for synthesis and catalysis and magnetic recyclability form the hallmark features of the heteronanostructure.

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Biosynthesis of Fe, Pd, and Fe–Pd bimetallic nanoparticles and their application as recyclable catalysts for [3 + 2] cycloaddition reaction: a comparative approach

Cited by 71 publications

References 64 publications

Magnetically Separable Iron Oxide Nanoparticles: An Efficient and Reusable Catalyst for Imino Diels–Alder Reaction

Magnetically Separable Iron Oxide Nanoparticles: An Efficient and Reusable Catalyst for Imino Diels–Alder Reaction

$$\hbox {Re}_{2}\hbox {O}_{7}$$ Re 2 O 7 -catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation

Sustainable Redox Chemistry Route to Multifaceted Fe‐Pd Heteronanostructure: Delving into the Synergistic Influence in Catalysis

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