Use of CuO encapsulated in mesoporous silica SBA-15 as a recycled catalyst for allylic C–H bond oxidation of cyclic olefins at room temperature

Samadi, Saadi; Ashouri, Akram; Ghambarian, Mehdi

doi:10.1039/c7ra02995k

Cited by 17 publications

(20 citation statements)

References 59 publications

(70 reference statements)

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“…To study the effect of the catalyst support on the catalytic synthesis, the model reaction was applied for the parent MOF (UiO-66-NH 2 ) and the modified MOF (UiO-66-NH 2 -Mlm). There was not observed any products after 24 h ( Table 2, entry 8,9). Therefore, the support did not show any synergic effect on…”

Section: Synthesis Of Arylamines and Benzimidazoles Bymentioning

confidence: 83%

“…The best reaction time was found to be 30 min. Using shorter time, the reaction was not completed, and using longer time, the reaction yield was almost constant ( Table 4, entries [6][7][8][9]. The effect of the catalyst amount on the reaction was also studied ( Table 4, entries 6 and 10-12), while the other parameters were kept constant.…”

Section: Synthesis Of 2-substituted Benzimidazolesmentioning

confidence: 99%

“…Copper as an abundant and inexpensive element, compared with noble metals (e.g. Pd), has been widely used for catalyzing organic reactions such as photodecarboxylation, click azide‐alkyne cycloaddition , C–C cross‐coupling reaction of Suzuki–Miyaura and Stille and Sonogashira–Hagihara , alkynylation of tetrahydroisoquinoline , C–O cleavage/C–N formation for synthesis of indazolo[3,2‐ b ]quinazolinones , allylic C–H oxidation of cyclic olefins , aerobic oxidation of alcohols , oxidative amidation of methylarenes , and also synthesis of carbonyl dibenzofurans , â‐enamino esters , ynones , quinoxalines , polysubstituted pyridines , and indole‐2‐carboxylic esters .…”

Section: Introductionmentioning

confidence: 99%

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Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Najari

Jafarzadeh

Bahrami

2019

Journal of Heterocyclic Chem

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A zirconium‐based metal–organic framework, UiO‐66‐NH2, modified by melamine (Mlm) was used as a support for CuO nanoparticles (NPs). Melamine offered a platform for uniform and homogeneous distribution of NPs on the surface of the frameworks and made a strong bonding to the NPs to avoid undesirable leaching. UiO‐66‐NH2‐Mlm/CuO NPs were used for the Buchwald–Hartwig C–N cross‐coupling reaction to synthesize arylated anilines from phenyl iodide, bromide, and chloride and primary and secondary amines in DMF at 110°C. The catalyst was also employed for the synthesis of 2‐substituted benzimidazole derivatives from various aromatic aldehydes and o‐phenylenediamine in the absence of an oxidant in EtOH at room temperature. The catalyst was recyclable and reusable for several times and exhibited good stability (examined by BET, XRD, and SEM–EDX) in reaction conditions.

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Section: Synthesis Of Arylamines and Benzimidazoles Bymentioning

confidence: 83%

Section: Synthesis Of 2-substituted Benzimidazolesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Najari

Jafarzadeh

Bahrami

2019

Journal of Heterocyclic Chem

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“…In general, various criteria concerning the metal species need to be considered prior to the incorporation of the metals into the support. For instance, allylic CH bond oxidation has been studied using different transition metals such as Cr, Co, Mn, and Cu . Among them, Cu grafted into the mesoporous silica via APTMS resulted in high catalytic efficiency due to its attractive properties, such as high yield, cost‐effectiveness, and recyclability, as well as its recovery ability .…”

Section: Potential Applicationsmentioning

confidence: 99%

Metal Species–Encapsulated Mesoporous Silica Nanoparticles: Current Advancements and Latest Breakthroughs

Kankala

Zhang

Liu

et al. 2019

Adv Funct Materials

124

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Despite their advantageous morphological attributes and attractive physicochemical properties, mesoporous silica nanoparticles (MSNs) are merely supported as carriers or vectors for a reason. Incorporating various metal species in the confined nanospaces of MSNs (M-MSNs) significantly enriches their mesoporous architecture and diverse functionalities, bringing exciting potentials to this burgeoning field of research. These incorporated guest species offer enormous benefits to the MSN hosts concerning the reduction of their eventual size and the enhancement of their performance and stability, among other benefits. Substantially, the guest species act through contributing to reduced aggregation, augmented durability, ease of long-term storage, and reduced toxicity, attributes that are of particular interest in diverse fields of biomedicine. In this review, the first aim is to discuss the current advancements and latest breakthroughs in the fabrication of M-MSNs, emphasizing the pros and cons, the confinement of various metal species in the nanospaces of MSNs, and various factors influencing the encapsulation of metal species in MSNs. Further, an emphasis on potential applications of M-MSNs in various fields, including in adsorption, catalysis, photoluminescence, and biomedicine, among others, along with a set of examples is provided. Finally, the advances in M-MSNs with perspectives are summarized.(2-5 nm), tunable sizes (50-150 nm), shapes (hexagonal, wormhole-like, cubic, and lamellar) and morphologies (spheres, helical fibers, tubules, gyroids, crystals, and numerous other hierarchical complex architectures), ease of surface functionalization (both interior as well as exterior), unique topology, colloidal and thermal stabilities, and high dispersity. [4] The exceptional topology of surfactant-templated MSNs makes them unique with desirable properties that can be obtained by controlling the preparation conditions, such as the reaction temperature, pH value, stirring speed, and type of silica source, as well as surfactant, among others. [4j,m,n,5] These advantages make the MSNs as versatile materials and ideal choice for catalysis, [6] adsorption, [7] optical devices, [4j] polymeric fillers, [8] and diverse biomedical applications including bio-imaging, [4r,t,u,9] biocatalysts, [10] biosensing, [11] tissue engineering, [4f ] and drug/ gene delivery accounting for targeted and controlled release systems. [3d,4i,o-t,v,12] With these significant advantages and attractive physicochemical properties, it is highly anticipated to harness the desirable and beneficial properties of MSNs through the incorporation of various metals and their respective conjugates for exploration in innovative applications with exceptional performance. [13] The encapsulated metal species in the confined nanospaces of MSNs (M-MSNs) not only significantly enrich the mesoporous architecture and functionalities of MSN, but also tend to overcome their intrinsic limitations, such as their poor suspension ability and stability, lack of intrig...

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“… 1 , 2 One way to prepare chiral heterogeneous catalysts is the immobilization of chiral ligands on inorganic supports such as mesoporous silica SBA-15. 3 − 6 In addition to having some special characteristics such as surface extension, uniform distribution, and adjustable pore diameter, SBA-15 has more advantages in comparison to other organic supports such as polymers, in which chemical stability in the reaction and mechanical resistance against the swelling in the solvent can be mentioned as examples. 7 − 9 …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts

2020

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A new class of recyclable supported chiral heterogeneous ligands has been synthesized by the reaction of functionalized mesoporous SBA-15 with aliphatic- and aromatic-substituted chiral amino oxazoline ligands. The obtained chiral heterogeneous ligands were characterized by several techniques such as Fourier transform infrared, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy, energy-dispersive X-ray spectroscopy, and BET–BJH. The application of these new heterogeneous ligands in copper-catalyzed asymmetric allylic oxidation of olefins by using perester showed better yields up to 95% and better enantioselectivities up to 96% compared to the corresponding homogeneous catalysts. These findings can be considered as an important step in the advancement of green chemistry. Investigation of the recyclability of the catalysts confirmed that they were easily recovered and reused eight times without significant losses in reactivity, yield, and enantioselectivity.

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Use of CuO encapsulated in mesoporous silica SBA-15 as a recycled catalyst for allylic C–H bond oxidation of cyclic olefins at room temperature

Abstract: CuO nanoparticles were deposited on SBA-15 in three routes. The catalytic activity of these catalysts was examined on the allylic C–H bond oxidation of cyclic olefins using tert-butyl p-nitrobenzoperoxoate as oxidant at room temperature.

Cited by 17 publications

References 59 publications

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Metal Species–Encapsulated Mesoporous Silica Nanoparticles: Current Advancements and Latest Breakthroughs

Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts

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Use of CuO encapsulated in mesoporous silica SBA-15 as a recycled catalyst for allylic C–H bond oxidation of cyclic olefins at room temperature

Abstract: CuO nanoparticles were deposited on SBA-15 in three routes. The catalytic activity of these catalysts was examined on the allylic C–H bond oxidation of cyclic olefins using tert-butyl p-nitrobenzoperoxoate as oxidant at room temperature.

Cited by 17 publications

References 59 publications

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH2 Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH2 Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Metal Species–Encapsulated Mesoporous Silica Nanoparticles: Current Advancements and Latest Breakthroughs

Synthesis of Chiral Allylic Esters by Using the New Recyclable Chiral Heterogeneous Oxazoline-Based Catalysts

Contact Info

Product

Resources

About

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles

Copper(II) Oxide Nanoparticles Impregnated on Melamine‐Modified UiO‐66‐NH₂ Metal–Organic Framework for C–N Cross‐Coupling Reaction and Synthesis of 2‐Substituted Benzimidazoles