Metal-supported carbon-based materials: opportunities and challenges in the synthesis of valuable products

Pérez‐Mayoral, Elena; Casilda, Vanesa Calvino; Soriano, Elena

doi:10.1039/c5cy01437a

Cited by 150 publications

(81 citation statements)

References 234 publications

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“…These energies were assigned to the Cl-Pd bonding energy from the oxime palladacycle 1. The band at 200.1 8 eV corresponded to the 2p3/2 aromatic-Cl bonding energy (Figure 3e) [62]. Thus, performing the palladation reaction using THF as solvent before immobilization onto GO led to the integral cyclopalladated species being supported.…”

Section: Resultsmentioning

confidence: 99%

“…Catalysts 2017, 7, 94 2 of 16 of palladacycles to graphene materials, with two studies having been reported so far using covalent immobilization strategies [62,63]. Very recently, we have shown that palladium nanoparticles (Pd NPs), supported on graphene and reduced graphene oxide, efficiently catalyze the Suzuki-Miyaura coupling between aryl bromides and potassium aryltrifluoroborates under aqueous and low loading conditions (0.1 mol % Pd) employing conventional or microwave heating [64].…”

Section: Resultsmentioning

confidence: 99%

“…In fact, Pd(0) has been previously detected when anchoring oxime palladacycles to different supports such as, 3-hydroxypropyltriethoxysilyl-functionalized MCM-41 [17] and 3-(aminomethyl)pyridinefunctionalized graphene oxide [62]. Figures 2 and 3 show the XPS spectra of 1 and 1-GO where the spectroscopic signature of palladium, carbon, oxygen, and nitrogen atoms has been determined [70][71][72] Regarding palladium (Figure 3a), the Pd3d XPS spectrum for 1 and 1-GO showed the corresponding binding energies at 337.70 (3d5/2) and 343.02 (3d3/2) eV and 337.62 (3d5/2) and 342.83 (3d3/2) eV, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…When unsupported palladacycle 1 was reduced with NaBH4 in the presence of GO ( Oxime palladacycles are considered reservoirs of highly active palladium nanoparticles [66][67][68]. Usually, PdNps supported on graphene materials are prepared by reduction of a Pd salt or Pd catalyst in the presence of the corresponding carbonaceous support [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. Then, we next turned our attention to the reduction of 1 with NaBH 4 and the catalytic activity of the supported PdNPs was thus obtained.…”

Section: Resultsmentioning

confidence: 99%

“…This type of catalyst has been mainly used in the Suzuki-Miyaura cross-coupling reaction [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62]. However, to the best of our knowledge, only very recently has some attention been paid to the immobilization of palladacycles to graphene materials, with two studies having been reported so far using covalent immobilization strategies [63,64].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

2017

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Palladacycles are highly efficient precatalysts in cross-coupling reactions whose immobilization on carbonaceous materials has been hardly studied. Herein, we report a detailed study on the synthesis and characterization of new oxime palladacycle-graphene oxide non-covalent materials along with their catalytic activity in the Suzuki-Miyaura reaction. Catalyst 1-GO, which has been fully characterized by ICP, XPS, TGA, and UV-Vis analyses has been demonstrated to be an efficient catalyst for the Suzuki-Miyaura coupling between aryl bromides and arylboronic acids using very low catalyst loadings (0.002 mol % of Pd) at room temperature under aqueous conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

2017

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Functionalization of multi‐walled carbon nanotubes by the baclofen drug to immobilize palladium nanoparticles and catalyze Sonogashira coupling reactions

Nazari

Hekmati

2019

Applied Organom Chemis

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The baclofen‐MWCNTs‐Pd nanocatalyst was synthesized through covalent grafting of baclofen molecules onto surface‐modified carbon nanotubes and immobilizing Pd nanoparticles by the baclofen ligands. The chemical structure of the produced nanocatalyst was studied by Raman spectroscopy, Fourier transform‐infrared spectroscopy, energy‐dispersive spectroscopy (EDS), elemental mapping and inductively coupled plasma analysis. Also, its surface morphology was determined using the scanning and transmission electron microscopy techniques. Furthermore, the obtained baclofen‐MWCNTs‐Pd nanocatalyst is demonstrated to exhibit very high activity as a heterogeneous phosphine‐free catalyst in Sonogashira cross‐coupling of aryl halides by giving good to excellent yields of different products. In addition, the nanocatalyst can be reused four times without any significant leaching or loss of activity.

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Cost‐effective bio‐derived mesoporous carbon nanoparticles‐supported palladium catalyst for nitroarene reduction and Suzuki–Miyaura coupling by microwave approach

Supriya¹,

Ananthnag²,

Shetti

et al. 2020

Applied Organom Chemis

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A new heterogeneous catalyst was synthesized by immobilizing Pd on areca nut kernel‐derived carbon nanospheres (CNSs). The CNSs, without any further activation processes, accommodated 3% of Pd on their surface. The new Pd/CNS material was used for the reduction of nitroarenes and Suzuki–Miyaura coupling of bromoarenes with aryl boronic acids. The reactions were conducted under microwave irradiation at 160 °C using 12 mol% of Pd/CNS (0.36% actual Pd content). The reduction of nitroarenes into their respective amino compounds was achieved in 10–20 min (conversion up to 100%); by contrast, the Suzuki–Miyaura reactions yielded up to 98% at 150 °C with 10 mol% of Pd/CNS catalyst. The products were identified using gas chromatography and nuclear magnetic resonance spectroscopy. The catalyst was isolated from reaction mixture and reused without any significant loss in the activity. Thus, the present work introduces one‐pot‐derived porous CNSs as efficient catalytic support to Pd, establishing an alternative to existing Pd/C in terms of cost and efficiency.

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Metal-supported carbon-based materials: opportunities and challenges in the synthesis of valuable products

Abstract: We summarize relevant applications and limitations of metal-supported carbons and nanocarbons in the synthesis of valuable products and the recent advances in this field.

Cited by 150 publications

References 234 publications

Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

Functionalization of multi‐walled carbon nanotubes by the baclofen drug to immobilize palladium nanoparticles and catalyze Sonogashira coupling reactions

Cost‐effective bio‐derived mesoporous carbon nanoparticles‐supported palladium catalyst for nitroarene reduction and Suzuki–Miyaura coupling by microwave approach

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