2765-23-3

Upstream product

• 91-20-3 naphthalene 
• 456-27-9 4-nitrobenzenediazonium tetrafluoroborate 
• 90-14-2 1-Iodonaphthalene 
• 586-78-7 para-nitrophenyl bromide 
• 13922-41-3 1-Naphthylboronic acid 
• 100-00-5 4-chlorobenzonitrile 
• 636-98-6 p-nitrobenzene iodide 
• 33397-22-7 tri(naphthalen-1-yl)bismuth 
• 24067-17-2 4-nitrophenylboronic acid 
• 1947-33-7 4-nitrobenzenediazonium 4-methylbenzenesulfonate 
• 1351445-39-0 N,N,N-trimethyl-1-naphthalenaminium trifluoromethanesulfonate 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 1415237-87-4 (PhCH₂CHC(COOMe)₂)GaCl₃ 
• 90-11-9 1-Bromonaphthalene 

Downstream Products

• 69505-30-2 2,4-Dichloro-1-(4-nitro-phenyl)-naphthalene 
• 69505-28-8 2,3-Dichloro-1-(4-nitro-phenyl)-naphthalene 
• 109810-72-2 N-(4-(naphthalen-1-yl)phenyl)acetamide 

Relevant academic research and scientific papers

Suzuki coupling reactions catalyzed by Schiff base supported palladium complexes bearing the vitamin B6 cofactor

Novel Schiff bases were synthesized by condensing aromatic amines with pyridoxal-5’-phosphate and characterized by using FT-IR, 1H NMR, and 13C NMR spectroscopic techniques. The resulting Schiff bases were utilized as bidentate ligands, coordinating via imine nitrogen and phenolate oxygen atoms, to stabilize palladium ions. Aryl substituents on imine nitrogen allowed for fine tuning of the stereoelectronic properties of the Schiff bases. The catalytic activity of the selected palladium complexes was investigated in the Suzuki cross-coupling reaction of a series of aryl halides with boronic acids in H2O/EtOH (1:1). Out of four complexes investigated in the cross-coupling reactions, Pd(L8)2, bearing a methoxy substituent on aryl imine, showed the highest activity at low catalyst loading. The scope of the reaction was also investigated with 26 samples.

Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction

A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy?(TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES)?analysis was used to determine the exact amount of Pd (0.33?wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki–Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K2CO3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339?h?1); in the presence of 1?mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 × 10–6?mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic Abstract: [Figure not available: see fulltext.]

Agro-Waste Generated Pd/CAP-Ash Catalyzed Ligand-Free Approach for Suzuki–Miyaura Coupling Reaction

Abstract: We converted agro-waste Custard Apple Peels (CAP) to ash via thermal treatment, on which Pd(OAc)2 was immobilized easily that produced a low-cost, highly efficient Pd/CAP-ash catalyst. The prepared catalyst was fully characterized by using FT-IR, SEM, EDX, XRF, DSC-TGA, BET, HR-TEM, and XPS techniques. The Pd/CAP-ash catalyst was conveniently applied for the Suzuki–Miyaura coupling reaction under external base free and ligand-free conditions in an aqueous-organic solvent to produce biphenyls in good to excellent yields. The main attraction of our protocol an application of palladium-supported agro-waste material which is easily recoverable and recyclable provides mono and bis-coupled derivatives in a short reaction time. Graphic Abstract: [Figure not available: see fulltext.].

Magnetite@MCM-41 nanoparticles as support material for Pd-N-heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction

The Magnetite@MCM-41@NHC@Pd catalyst was obtained with Pd metal bound to the NHC ligand anchored to the surface of Fe3O4@MCM-41. It was characterized by Fourier transform infrared (FTIR) spectroscopy, transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy disperse X-ray analysis (EDX), thermogravimetric analysis (TGA), differential thermal analysis (DTA), and scanning electron microscopy (SEM). The amount of Pd in the Magnetite@MCM-41@NHC@Pd was measure by inductively coupled plasma–optical emission spectroscopy (ICP-OES) analysis. The catalytic activity of Magnetite@MCM-41@NHC@Pd heterogeneous catalyst done on Suzuki–Miyaura reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions afforded excellent yields and up to 408404 Turnover Frequency (TOF) h?1 in the presence of 2 mg of Magnetite@MCM-41@NHC@Pd catalyst (0.0564 mmol g?1, 0.01127 mmol% Pd) at room temperature in 2-propanol/H2O (1:2). Moreover, Magnetite@MCM-41@NHC@Pd catalyst was recover by applying the magnet and reused for another reaction. The catalyst showed excellent structural and chemical stability and reused ten times without a substantial loss in its catalytic performance.

N-heterocyclic carbene Pd(II) complex supported on Fe3O4@SiO2: Highly active, reusable and magnetically separable catalyst for Suzuki-Miyaura cross-coupling reactions in aqueous media

A new type magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was fabricated and characterized by Fourier Transform Infrared (FTIR) spectroscopy, Transmission Electron Microscopy (TEM), X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Energy Disperse X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA), and Scanning Electron Microscopy (SEM). The loading amount of Palladium (Pd) to magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs was measured by Inductively Coupled Plasma-Optical Emission Spectroscopy (ICP-OES) analysis. The catalytic activity of magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs heterogeneous catalyst was examined on Suzuki-Miyaura cross-coupling reactions of aryl halides with different substituted arylboronic acid derivatives. All coupling reactions yielded excellent results and high TOF (up to 76528 h?1) in the presence of 2 mg of Fe3O4@SiO2@NHC@Pd-MNPs catalyst (0.0197 mmolg?1, 0.00394 mmol%Pd) at 80 °C in 2-propanol/H2O (1:2). In addition, the magnetic nano Fe3O4@SiO2@NHC@Pd-MNPs catalyst was easily recovered by using an external Nd-magnet and reused for the Suzuki cross-coupling reactions. The catalyst showed strong structural and chemical stability and was reused six times without losing its catalytic activity substantially.

Design of Benzimidazolyl Phosphines Bearing AlterableP,OorP,N-Coordination: Synthesis, Characterization, and Insights into Their Reactivity

A new series of hemilabile benzimidazolyl phosphines is reported. Entities in this ligand family can be easily assembled and prepared on a large scale via a simple one-pot procedure. X-ray crystallographic analyses show that the Pd metal center can coordinate in different fashions, where it relies on the size of the ?PR2group. With the same ligand scaffold, the ligand having a ?PCy2moiety displays better efficiency in expediting aromatic C-C bond-coupling reactions, while the ligand associated with a ?P-t-Bu2group, in contrast, promotes C-N bond-forming reactions.

C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex

We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.

Pd/REOs catalysts applied to the Suzuki-Miyaura coupling. A comparison of their catalytic performance and reusability

Two new palladium catalysts based on rare earth oxide supports, namely, Pd/Dy2O3 and Pd/Yb2O3 were prepared by the incipient wetness impregnation method, followed by calcination at 600 °C. Both compounds, which were fully characterized, were tested as catalysts in the Suzuki-Miyaura reaction and their catalytic activity was compared with that of already known Pd/La2O3, Pd/CeO2, Pd/Pr6O11, Pd/Sm2O3, and Pd/Gd2O3. It has been found that the nature of the support strongly affects the catalytic activity. The scope of the catalytic protocol was investigated and quantitative yields of the coupling products (21 examples are reported) were always observed using a low metal amount (0.05 mol%). A systematic investigation on the reusability of the entire set of catalytic systems has been carried out. All catalysts showed to be successfully recyclable, and also in this case the nature of the rare earth element is crucial. The highest reusability was observed for catalysts Pd/CeO2 and Pd/Sm2O3.

Synthesis of a class of binaphthyl monophosphine ligands with a naphthofuran skeleton and their applications in Suzuki-Miyaura coupling reactions

A series of new monophosphine ligands containing a naphthofuran skeleton have been prepared, characterized and evaluated in palladium-catalyzed Suzuki-Miyaura coupling reactions. Using Pd2(dba)3-L6 as the catalyst the reactions were performed with high catalytic activity under mild reaction conditions and the desired coupling products were obtained in good to excellent yields. The new catalyst system also showed broad substrate adaptability and practicality for gram-scale production.

[4 + 2] Annulation of Donor-Acceptor Cyclopropanes with Acetylenes Using 1,2-Zwitterionic Reactivity

A new process for the [4 + 2] annulation of donor-acceptor cyclopropanes with acetylenes under the effect of anhydrous GaCl3 using 1,2-zwitterion reactivity was elaborated. The reaction opens access to substituted dihydronaphthalenes, naphthalenes, and other fused carbocycles. The direction of the reaction can be efficiently controlled by temperature.