A facile preparation of palladium Schiff base complex supported into MCM-41 mesoporous and its catalytic application in Suzuki and Heck reactions

Nikoorazm, Mohsen; Ghorbani‐Choghamarani, Arash; Jabbari, Arida

doi:10.1007/s10934-016-0154-7

Cited by 36 publications

(12 citation statements)

References 36 publications

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“…The peaks at around 1.5° and 2.4° in the small-angle XRD pattern could be assigned to the typical plane of MSN, thus confirming the successful preparation of mesoporous MSN (Figure S5). For the Pd-containing samples, the peaks centered at 2θ = 39.4°, 46.1°, 68.3°, and 81.1° in the wide-angle XRD pattern belong to the 111, 200, 220, and 311 diffraction maxima of metallic Pd characterized by its face-centered cubic structure, respectively. , The disappearance of the characteristic diffraction peaks at 1.5° and 2.4° in small-angle XRD is related to the destruction of the regular mesoporous structure of MSN caused by the incorporation of Pd, which indicates the filling of the MSN pore channels by Pd NPs. , The specific surface areas and porosities of the resultant materials were measured by the N 2 adsorption/desorption experiments. The curve of MSN represents a type-IV isotherm pattern, indicating mesoporosity .…”

Section: Resultsmentioning

confidence: 93%

Surface-Functionalized Mesoporous Nanoparticles as Heterogeneous Supports To Transfer Bifunctional Catalysts into Organic Solvents for Tandem Catalysis

Hübner

Wang

Zhang

et al. 2018

ACS Appl. Nano Mater.

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The combination of chemo-and biocatalysts offers a powerful platform to address synthetic challenges in chemistry, particularly in synthetic cascades. However, transferring both of them into organic solvents remains technically difficult due to the enzyme inactivation and catalyst precipitation. Herein, we designed a facile approach using functionalized mesoporous silica nanoparticles (MSN) to transfer chemo-and biocatalysts into a variety of organic solvents. As a proof-of-concept, two distinct catalysts, palladium nanoparticles (Pd NPs) and Candida antarctica lipase B (CalB), were stepwise loaded into separate locations of the mesoporous structure, which not only provided catalysts with heterogeneous supports for the recycling but also avoided their mutual inactivation. Moreover, mesoporous particles were hydrophobized by surface alkylation, resulting in a tailor-made particle hydrophobicity, which allowed bifunctional catalysts to be dispersed in eight organic solvents. Eventually, these attractive material properties provided the MSN-based bifunctional catalysts with remarkable catalytic performance for cascade reaction synthesizing benzyl hexanoate in toluene. On a broader perspective, the success of this study opens new avenues in the field of multifunctional catalysts where a plethora of other chemo-and biocatalysts can be incorporated into surface-functionalized materials ranging from soft matters to porous networks for synthetic purpose in organic solvents.

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Section: Resultsmentioning

confidence: 93%

Surface-Functionalized Mesoporous Nanoparticles as Heterogeneous Supports To Transfer Bifunctional Catalysts into Organic Solvents for Tandem Catalysis

Hübner

Wang

Zhang

et al. 2018

ACS Appl. Nano Mater.

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“…[10] So far, many organic acid/base catalysts and their bifunctional systems have been successfully immobilized on various solid supports and have shown impressive catalytic performances in various reactions. [11][12][13][14][15][16][17][18][19][20] Over the past decades, magnetic nanoparticles have been a great topic for research on a wide range of applications, including environmental remediation, [21] targeted drug delivery, [22] and catalysis. [23][24][25] Among these MNPs, Fe 3 O 4 has been identified as the most widely and the ideal and vastly used support in a catalyst.…”

Section: Introductionmentioning

confidence: 99%

“…Though there are different types of catalyst available, yet designing a heterogeneous catalyst has been important for organic reactions because the heterogeneous catalysts have several advantages; (i) recoverability, (ii) reusability, (iii) the use of catalytic amount, (iv) value of the metal leaching into the reaction solution after reuse can be tolerated, (v) not to undergo the structural degradation [10] . So far, many organic acid/base catalysts and their bifunctional systems have been successfully immobilized on various solid supports and have shown impressive catalytic performances in various reactions [11–20] …”

Section: Introductionmentioning

confidence: 99%

Immobilization of Polyoxometalate onto Modified Magnetic Nanoparticles: A New Catalyst for the Synthesis of Dihydropyranopyrazole Derivatives

et al. 2021

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A new nanocatalyst Fe3O4@carbon@polyoxometalate (Fe@C@Mo6O18) consisting of a cluster of Fe3O4 nanoparticles as core, a carbon layer as inner shell, and a Lindqvist type polyoxometalate as the outer shell was prepared. The prepared nanocatalyst structure was characterized by energy dispersive X‐ray (EDX), scanning electron microscopy (SEM), vibration sample magnetometer (VSM), thermogravimetric analysis (TGA), and Fourier transform infrared (FT‐IR) spectroscopy techniques and their catalytic activity was evaluated for the synthesis of dihydropyranopyrazole derivatives. The results were excellent regarding the high yield of the products and short reaction time. The new nanocatalyst showed good recoverability with a significant loss of activity and selectivity within successive runs. Most importantly, these materials can be easily recovered by simple magnetic separation.

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“…In particular, imines synthesized by the condensation of salicyl-aldehyde with an aliphatic or an aromatic diamine are commonly known as SALEN or SALOPHEN ligands, respectively, and these ligands can be employed as N 2 O 2 ligands for the preparation of palladium-based catalysts. Recently, homogeneous/immobilized Pd-SALEN and -SALOPHEN catalysts have been reported as excellent catalysts for use in the Mizoroki–Heck [31,41,42,43,44] and Suzuki–Miyaura [44,45,46,47,48] C–C coupling reactions, due to their high selectivity, air- and moisture-stability, and relatively low toxicity.…”

Section: Introductionmentioning

confidence: 99%

Mesoporous Palladium N,N’-Bis(3-Allylsalicylidene)o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction

et al. 2019

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Palladium N,N’-bis(3-allylsalicylidene)o-phenylenediamine complex (PdAS) immobilized onto mesoporous polymeric methyl acrylate (MA) based resins (PdAS(x)-MA, x = 1, 2, 5, or 10 wt.%) were successfully prepared as heterogeneous catalysts for the Heck reaction. The catalysts were synthesized via radical suspension polymerization using PdAS as a metal chelate monomer, divinylbenzene and MA as co-monomers. The effect of the PdAS(x) content on the physicochemical properties of the resins is also reported. The catalysts were characterized by using a range of analytical techniques. The large surface area (>580 m2·g−1) and thermal stability (up to 250 °C) of the PdAS(x)-MA materials allows their application as catalysts in the C–C coupling reaction between iodobenzene and MA in the presence of trimethylamine at 120 °C using DMF as the solvent. The PdAS(10)-MA catalyst exhibited the highest catalytic performance with no significant catalytic loss being observed after five reuses, thereby indicating excellent catalyst stability in the reaction medium.

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A facile preparation of palladium Schiff base complex supported into MCM-41 mesoporous and its catalytic application in Suzuki and Heck reactions

Cited by 36 publications

References 36 publications

Surface-Functionalized Mesoporous Nanoparticles as Heterogeneous Supports To Transfer Bifunctional Catalysts into Organic Solvents for Tandem Catalysis

Surface-Functionalized Mesoporous Nanoparticles as Heterogeneous Supports To Transfer Bifunctional Catalysts into Organic Solvents for Tandem Catalysis

Immobilization of Polyoxometalate onto Modified Magnetic Nanoparticles: A New Catalyst for the Synthesis of Dihydropyranopyrazole Derivatives

Mesoporous Palladium N,N’-Bis(3-Allylsalicylidene)o-Phenylenediamine-Methyl Acrylate Resins as Heterogeneous Catalysts for the Heck Coupling Reaction

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