Sulfonated Core‐Shell Magnetic Nanoparticle (Fe3O4@SiO2@PrSO3H) as a Highly Active and Durable Protonic Acid Catalyst; Synthesis of Coumarin Derivatives through Pechmann Reaction

Esfahani, Farhad Kabiri; Zareyee, Daryoush; Yousefi, Reza

doi:10.1002/cctc.201402547

Cited by 42 publications

(14 citation statements)

References 58 publications

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“…Compared to previous reports [25,[42][43][44][45][46][52][53][54][55][56][57][58], this study also demonstrated that the surface area of the catalytic systems can be manipulated by the synthetic methodology. As can be observed from the obtained data, the acidic SiO 2 catalyst varies in the surface area in comparison to the one prepared from TEOS and displays more activity towards the Pechmann reaction.…”

Section: Methodsmentioning

confidence: 41%

“…Meanwhile, Zareyee and Serehneh [43] employed CMK-5 adapted by sulfonic acid as a catalyst to synthesize coumarin from substituted phenols and ethylacetoacetate. Other reports explored successful attempts of using sulfonated magnetic nanoparticles in forming coumarin derivatives [44,45]. Sulfonated mesoporous silica has also been utilized to prepare 7-hydroxy-4-methyl coumarin [46].…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

et al. 2018

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New modified acidic catalysts were prepared from the treatment of silica, titania and silica prepared from hydrolyzed tetraethyl orthosilicate (TEOS) with sulfuric and phosphoric acid. The sulfated and phosphated silica synthesized from TEOS were calcined at 450 and 650 • C. These catalysts were characterized by X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FTIR), transmission electron microscope (TEM), and scanning electron microscope (SEM). The surface areas, total pore volume, and mean pore radius of the acidic catalysts were investigated, while the pore size distribution was determined by the Barrett, Joyner and Halenda (BJH) method. The catalytic activity of the sulfated and phosphated silica and/or titania were examined with the Pechmann condensation reaction, in which different phenols reacted with ethyl acetoacetate as a neat reaction to obtain the corresponding coumarin derivatives. The results indicated that the treatment of the catalysts with sulfuric or phosphoric acid led to a decrease in the phases' crystallinity to a certain degree. The morphology and the structure of the acidified catalysts were examined and their particle size was calculated. Furthermore, the amount of the used catalysts played a vital role in controlling the formation of the products as well as their performance was manipulated by the number and nature of the active acidic sites on their surfaces. The obtained results suggested that the highest catalytic conversion of the reaction was attained at 20 wt % of the catalyst and no further increase in the product yield was detected when the amount of catalyst exceeded this value. Meanwhile the phenol molecules were a key feature in obtaining the final product.

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Section: Methodsmentioning

confidence: 41%

Section: Introductionmentioning

confidence: 99%

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

et al. 2018

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“…Based on our experience in design and application of novel nanostructured catalysts in recent years, [17,[60][61][62][63][64][65] the nanocatalyst CNC-AMPD-Pd was prepared by route depicted in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent‐free synthesis of coumarin derivatives via von Pechmann condensation

Mirosanloo

Zareyee

Khalilzadeh

2018

Applied Organom Chemis

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2-Amino pyrimidine nanocellulose-supported Palladium nanoparticles (CNC-AMPD-Pd) as a novel bio supported nanocatalyst was prepared and characterized by ICP-AES, FT-IR, XRD, SEM, TEM, TGA and EDX techniques. The nanocatalyst demonstrated outstanding performance in Pechmann condensation between different substituted phenols and ethyl acetoacetate to obtain coumarin derivatives in good to excellent yields. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst and solvent-free reaction conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup.

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“…[28][29][30][31][32] Nowadays with the advancement of nanoscience, magnetic nanoparticles (MNPs) as an effective heterogeneous catalyst have been widely synthesized and used efficiently in various organic syntheses. [33][34][35][36][37][38][39][40][41] In addition to common properties of all nanoparticles such as the high surface area, as well as chemical and thermal stability, MNPs could be separated easily from reaction mixture using an external magnet. Immobilization of various shells such as silica and carbon on the surface of MNPs protects them against agglomeration and improves the chemical stability of MNps from environmental degradation and also provide an appropriate surface for further modification while the magnetic core causes easy separation using an external magnet.…”

Section: Introductionmentioning

confidence: 99%

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Ghavidel

Mirza

Soleimani‐Amiri

et al. 2020

J Chinese Chemical Soc

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A green synthesis of functionalized 4H-chromenes using one-pot, threecomponent reaction of salicylaldehyde (1), active methylene (2), and carbonbased nucleophile (3) using Fe 3 O 4 @CONa nanoparticles in water has been performed at 60 C. The Fe 3 O 4 @CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst and solvent, short reaction time, high product yields, as well as simple work-up procedure were found as some advantages of this methodology. The density functional theory calculations were applied to all-inclusive perception of the one-pot, three-component reaction mechanism. The most reactions progressed through the following route: (a) nucleophilic addition of 2 to 1; (b) ring closing, dehydration; (c) nucleophilic substitution of 3 (2-naphtol, 4-hydroxycumarin) to intermediate. Sometimes mechanism mutated to: (a) nucleophilic addition of 3 (indole, 2-methylindole) to 1, and dehydration; (b) nucleophilic addition of 2 to intermediate; and (c) ring closing, and dehydration. The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms. Theoretical study could be so helpful to pick out suitable reactants of the reaction.

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Sulfonated Core‐Shell Magnetic Nanoparticle (Fe₃O₄@SiO₂@PrSO₃H) as a Highly Active and Durable Protonic Acid Catalyst; Synthesis of Coumarin Derivatives through Pechmann Reaction

Cited by 42 publications

References 58 publications

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

Catalytic Activity of Sulfated and Phosphated Catalysts towards the Synthesis of Substituted Coumarin

Recyclable cellulose nanocrystal supported Palladium nanoparticles as an efficient heterogeneous catalyst for the solvent‐free synthesis of coumarin derivatives via von Pechmann condensation

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

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