Iron–Organic Framework Nanoparticle-Supported Tungstosilicic Acid as a Catalyst for the Biginelli Reaction

Zhang, Hong; Hu, Qiang; Liu, Jutao; Zhang, Penghui; Fu, Shuaishuai; Wu, Shang

doi:10.1021/acsanm.2c03906

Cited by 10 publications

(9 citation statements)

References 53 publications

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“…The activity of our catalysts toward the 4a product has been compared with that of other solid acid catalysts, collecting relevant data in Table S3 [ 55 , 56 , 57 , 58 ]. The performance of HNTs derivatives is generally lower than that of other reported catalysts.…”

Section: Resultsmentioning

confidence: 99%

Halloysite Nanotubes as Bimodal Lewis/Brønsted Acid Heterogeneous Catalysts for the Synthesis of Heterocyclic Compounds

Mateos

Carraro

2023

Nanomaterials

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Halloysite nanotubes can be used for the preparation of solid catalysts. Owing to their natural availability at low-cost as well as to their large and easy-to-functionalize surface, they can be conveniently activated with mineral acids or derivatized with acidic groups. Nevertheless, the use of HNTs as catalysts in complex transformations is still limited. Herein, we report two strategies to utilize HNT-based materials as solid acidic catalysts for the Biginelli reaction. To this aim, two methods for increasing the number of acidic sites on the HNTs were explored: (i) the treatment with piranha solution (Pir-HNTs) and (ii) the functionalization with phenylboronic acid (in particular with benzene-1,4-diboronic acid: the sample is denoted as HNT-BOA). Interestingly, both strategies enhance the performance of the multicomponent reaction. Pir-HNTs and HNT-BOA show an increased reactivity (72% and 89% yield, respectively) in comparison with pristine HNTs (52%). Additionally, Pir-HNTs can be reused up to five times without significant performance loss. Moreover, the method also displays good reaction scope, as demonstrated by the preparation of 12 different 3,4-dihydropyrimidinones in up to 71% yield. Therefore, the described strategies are promising for enhancing the acidity of the HNTs as catalysts for the organic reaction.

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Section: Resultsmentioning

confidence: 99%

Halloysite Nanotubes as Bimodal Lewis/Brønsted Acid Heterogeneous Catalysts for the Synthesis of Heterocyclic Compounds

Mateos

Carraro

2023

Nanomaterials

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“…In 2022, Wu and co-workers synthesized a metal-organic framework named TSA/MIL-88B using a tungstosilicic acid nanocatalyst via a post-synthetic modification method that was used effectively for Biginelli reaction. 35 The combination of TSA and MIL-88B was verified with FT-IR and XPS spectra. They carried out the reaction using benzaldehyde, ethyl acetoacetate, and urea as model substrates and TSA/MIL-88B as catalyst in EtOH as solvent at 80 C for 4 h, and achieved a high yield of 97% (Scheme 14).…”

Section: S C H E M E 1mentioning

confidence: 94%

“…In 2022, Wu and co‐workers synthesized a metal‐organic framework named TSA/MIL‐88B using a tungstosilicic acid nanocatalyst via a post‐synthetic modification method that was used effectively for Biginelli reaction 35 . The combination of TSA and MIL‐88B was verified with FT‐IR and XPS spectra.…”

Section: Using Ethanol As Solventmentioning

confidence: 99%

Advances in Biginelli reaction: A comprehensive review

Chandravarkar,

Aneeja,

Anilkumar

2023

Journal of Heterocyclic Chem

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The Biginelli reaction, a conventional three‐component reaction provides 3,4‐dihydropyrimidin‐2(1H)‐ones/thiones via one‐pot acid catalyzed cyclocondensation of an aldehyde, a β‐keto ester, and urea or thiourea. Dihydropyrimidones are well‐known scaffolds having a wide range of pharmacological activities. So far classical Biginelli reaction has witnessed several modification and studies are still continuing in this field to develop greener and efficient methodologies. In this review, we summarize the recent advances in Biginelli reaction covering literature from 2020 to 2023.

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“…However, the results of the second reduction approved the effective binding of Pd NPs to the outer materials. 34,40,42 Moreover, after studying the samples' pore sizes and pore volumes before (Fe 3 O 4 @MON) and after palladium immobilization (Fe 3 O 4 @ MON-Pd-1), characteristic trends were observed. Based on the pore size diagrams (Figure S8), core−shell Fe 3 O 4 @MON and Fe 3 O 4 @MON-Pd-1 showed 2.30 and 2.15 nm pore sizes, and pore volumes decreased from 0.188 to 0.155 cm 3 /g, respectively.…”

Section: Xrd and Bet Analysesmentioning

confidence: 97%

Size-Dependent Catalytic Activity of Palladium Nanoparticles Decorated on Core–Shell Magnetic Microporous Organic Networks

Khojastehnezhad,

Gamraoui,

Jafari

et al. 2023

ACS Appl. Nano Mater.

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It is of supreme importance to develop recyclable and green heterogeneous catalysts due to their potential to reduce environmental impact and reduce costs associated with their use. Hence, in this research, an initial development was made of a core−shell magnetic structure composed of Fe 3 O 4 and a microporous organic network (MON), followed by the physical absorption of palladium nanoparticles (NPs) onto the outer surface of this shell substance. The results of TEM and EDX analyses indicated that Pd NPs of varying sizes, which were produced by using different reducing agents, were evenly bound to the MON shell materials. The use of PiFM and XPS analyses provided evidence that there was effective bonding between Pd nanoparticles and the amine groups present on the surface of MON materials. Besides, the successful immobilization of palladium NPs was also approved by N 2 adsorption/desorption analyses with the decrease of the surface from 328 to 227 m 2 /g after palladium inclusion. The prepared nanoheterogeneous catalysts can catalyze the C−C formation in mild conditions, green solvents, and short reaction times with good to excellent yields. The results revealed that the catalyst with smaller palladium NPs sized 1−5 nm and in medium abundance has better catalytic performance toward C−C formation, compared to those with bigger Pd NPs sized 5−15 nm and in both low and high Pd contents.

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Iron–Organic Framework Nanoparticle-Supported Tungstosilicic Acid as a Catalyst for the Biginelli Reaction

Cited by 10 publications

References 53 publications

Halloysite Nanotubes as Bimodal Lewis/Brønsted Acid Heterogeneous Catalysts for the Synthesis of Heterocyclic Compounds

Halloysite Nanotubes as Bimodal Lewis/Brønsted Acid Heterogeneous Catalysts for the Synthesis of Heterocyclic Compounds

Advances in Biginelli reaction: A comprehensive review

Size-Dependent Catalytic Activity of Palladium Nanoparticles Decorated on Core–Shell Magnetic Microporous Organic Networks

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