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Relevant academic research and scientific papers

Templating effect of carbon nanoforms on highly cross-linked imidazolium network: Catalytic activity of the resulting hybrids with Pd nanoparticles

Two different carbon nanoforms (CNFs), namely multi-walled carbon nanotubes (MWCNTs) and carbon nanohorns (CNHs), have been chosen as support for the direct polymerization of a bis-vinylimidazolium salt. Transmission electron microscopy analyses revealed a templating effect of the CNFs on the growth of the polymeric network, which perfectly covers their whole surfaces creating a cylindrical or spherical coating for MWCNTs and CNHs, respectively. Subsequently, the CNFs-polyimidazolium have been used as stabilizers for Pd nanoparticles (Pd NPs), and the obtained materials have been characterized by means of analytical and spectroscopic techniques and then employed as easily recoverable and recyclable catalysts for Suzuki and Heck reactions. Quantitative conversions have been obtained in almost all the explored reactions, even employing low loading of catalyst (down to 0.007 mol%). Suzuki reactions were carried out in pure water under aerobic conditions. Both materials showed excellent activity and recyclability for the investigated C-C coupling reactions, with the CNHs-based material resulting slightly more active than the MWCNTs-based one due to a higher superficial exposure of Pd NPs.

Palladium Complexes with Phenoxy- And Amidate-Functionalized N-Heterocyclic Carbene Ligands Based on 3-Phenylimidazo[1,5- a]pyridine: Synthesis and Catalytic Application in Mizoroki-Heck Coupling Reactions with Ortho-Substituted Aryl Chlorides

Mononuclear and tetranuclear palladium complexes with functionalized "abnormal"N-heterocyclic carbene (aNHC) ligands based on 3-phenylimidazo[1,5-a]pyridine were synthesized. All of the new complexes were structurally characterized by single-crystal X-ray diffraction studies. The new complexes were applied in the Mizoroki-Heck coupling reaction of aryl chlorides with alkenes in neat n-tetrabutylammonium bromide (TBAB). The mononuclear palladium complex with a tridentate phenoxy- and amidate-functionalized aNHC ligand displayed activity superior to that of the palladium complex with a bidentate amidate-functionalized aNHC ligand. The new tetranuclear complex with the tridentate ligand displayed the best activities, capable of the activation of deactivated aryl chlorides as substrates with a low Pd atom loading. Even challenging sterically demanding ortho-substituted aryl chlorides were successfully utilized as substrates. The studies revealed that the robustness of the catalyst precursor is crucial in delivering high catalytic activities. Also, the promising use of tetranuclear palladium complexes with functionalized aNHC ligands as the catalyst precursors in the Mizoroki-Heck coupling reaction in neat TBAB was demonstrated.

Facile synthesis of a recyclable Pd-rGO/CNT/CaFe2O4 nanocomposite with high multifunctional photocatalytic activity under visible light irradiation

We report a facile method to synthesize a magnetically separable Pd-rGO/CNT/CaFe2O4 photocatalyst. The incorporation of CNTs into rGO can form a conductive network structure to bridge the gaps between rGO sheets. This conductive netw

A tailored polymeric cationic tag-anionic Pd(ii) complex as a catalyst for the low-leaching Heck-Mizoroki coupling in flow and in biomass-derived GVL

The [PdCl4]2- palladium complex has been immobilized on a polystyrene-type resin loaded with pincer-type imidazolium ionic tag binding sites. The catalytic system (Pd(ii)-POLI-TAG) has proved to be highly active in the definition of an efficient protocol for the Heck-Mizoroki coupling reaction under batch and flow conditions. Importantly, it is shown to be highly robust in combination with a safe non-toxic reaction medium, i.e. biomass-derived GVL, since it could be reused for multiple runs without significantly losing its activity.

Tetranuclear Palladium Complexes of Abnormal N-Heterocyclic Carbene Ligands and their Catalytic Activities in Mizoroki-Heck Coupling Reaction of Electron-Rich Aryl Chlorides

Based on the ligand scaffold of an imidazolyl/benziimidazolyl moiety and a N-CH2C(=O)NHPh substituent, two series of ligand precursors with ortho hydroxy groups incorporated on the N-phenyl rings were prepared. The structural fine tuning of the ligand scaffold allowed the synthesis of tetranuclear palladium complexes with abnormal N-heterocyclic carbene (aNHC) ligands. For precursors with C2-methyl blocking groups, pyridine-assisted C?H bond activation led to the formation of mononuclear tridentate palladium aNHC complexes or tetranuclear complexes with tridentate CNO donors. Representative mononuclear and tetranuclearpalladium aNHC complexes were structurally characterized by X-ray diffraction studies, revealing very short Pd?C bond distances. The tetranuclear palladium aNHC complexes were very effective in catalyzing Mizoroki-Heck coupling reaction, and were capable of employing a range of aryl chlorides including deactivated substrates with low palladium loading of 0.2 mol%. (Figure presented.).

An efficient Pd-NHC catalyst system in situ generated from Na2PdCl4 and PEG-functionalized imidazolium salts for Mizoroki-Heck reactions in water

Three PEG-functionalized imidazolium salts L1-L3 were designed and prepared from commercially available materials via a simple method. Their corresponding water soluble Pd-NHC catalysts, in situ generated from the imidazolium salts L1-L3 and Na2PdCl4 in water, showed impressive catalytic activity for aqueous Mizoroki-Heck reactions. The kinetic study revealed that the Pd catalyst derived from the imidazolium salt L1, bearing a pyridine-2-methyl substituent at the N3 atom of the imidazole ring, showed the best catalytic activity. Under the optimal conditions, a wide range of substituted alkenes were achieved in good to excellent yields from various aryl bromides and alkenes with the catalyst TON of up to 10,000.

An efficient trifunctional benzhydrazone ligated Pd(II) complex for Heck reaction of aryl bromides

Synthesis of air and thermally stable trifunctional O, N, and O-terdentate benzhydrazone Pd(II) complex is reported and characterized by elemental analysis, spectral methods, and single crystal X-ray crystallographic technique. The new and reusable homogeneous catalyst has been effectively applied to the Mizoroki-Heck reaction of activated and deactivated aryl bromides with various olefins under mild reaction conditions in good to excellent yields up to 99%.

Pd nanoparticles immobilized on Fe3O4 @ poly(ethylene glycol) bridged amine functionalized imidazolium ionic liquid: A magnetically separable catalyst for heck in water

A palladium-based catalyst supported on novel Fe3O4 @ Poly(ethylene glycol) bridged amine functionalized imidazolium ionic liquid (Fe3O4@PEG-AIm-NH2- IL) was successfully prepared by a facile method. The catalyst was characterized by FT-IR, TEM, VSM, XRD, XPS and TGA-DSC, which showed high activity and stability for the Heck reaction in pure water. Furthermore, the catalyst could be recovered in a facile manner from the reaction mixture and recycled five times without any loss in activity.

Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Palladium (10 wt%) on a highly cross-linked imidazolium-based material was used as catalyst in 0.1 mol% in the Heck reaction between several alkenes and aryl iodides. Products were obtained from good to high yields. Deeper investigations showed a release of Pd species in solution and their capture by the imidazolium-based support. When a sixfold amount of support was employed the re-captured Pd species (0.5-0.6 wt%) were not anymore catalytically active. This result represents a new interesting aspect of this work since the highly cross-linked imidazolium-based material can act also as Pd scavenger avoiding the release of the metal in solution. Important differences between Heck and Suzuki reactions have been evidenced when the reactions were carried out in the presence of the scavenging support.

Nickel(II) thiosemicarbazone complex catalyzed Mizoroki-Heck reaction

Convenient synthesis of a new square planar nickel(II) naphthaldehyde thiosemicarbazone complex has been described. The composition of the complex has been established by elemental analysis, spectral methods, and single crystal X-ray crystallography. The