49602-47-3Relevant academic research and scientific papers
A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
Walker, Shawn D.,Barder, Timothy E.,Martinelli, Joseph R.,Buchwald, Stephen L.
, p. 1871 - 1876 (2004)
Unprecedented scope, reactivity, and stability are displayed by a new catalyst system. This was demonstrated with general and efficient syntheses of sterically hindered (hetero)biaryls (see examples shown), mild coupling reactions of alkyl boron derivatives, and rapid coupling reactions of aryl chlorides at room temperature.
Magnetic nanoparticles supported N-heterocyclic palladium complex: Synthesis and catalytic evaluations in Suzuki cross-coupling reaction
Dong, Yahao,Xue, Fengjun,Wei, Yuping
, (2021/03/04)
Because of the robustness and magnetic properties, the magnetic materials are promising and alternative candidate for the fabrication of noble metal in chemical catalysis from the viewpoint of green chemistry. Accordingly, an eco-friendly magnetic palladium catalyst loaded on N-Methylimidazole functionalized Fe3O4@SiO2 nanoparticles (Fe3O4@SiO2-NMIM-Pd) has been designed and prepared in the present work. The resultant composite exhibited excellent catalytic activity towards the Suzuki cross-coupling reaction for the synthesis of the corresponding biaryls in good to excellent yields (up to 96%) under aerobic conditions. In particular, this catalyst could be easily recovered through magnetic separation in a few cycles. The as-prepared palladium complex showed advantages including high thermal stability, low toxicity, moisture and oxygen insensitivities in Suzuki reactions. More importantly, this study presents a catalysis system, which will provide the magnetic materials access to the potential applications in a wide range of green organic catalysis.
Preparation and characterization of a Cu complex based on 2,2′-bipyrimidine as a recyclable metal-organic framework for Suzuki coupling
Kiasadegh, Mehdi,Liu, Hongmei,Liu, Ming
, (2021/12/31)
A Cu complex based on 2,2′-bipyrimidine ([CuBpm·2H2O]n) as a recyclable metal-organic framework (MOF) was used for the synthesis of biaryl derivatives by the Suzuki coupling reaction. The Suzuki reaction was performed with mixing of aryl halides with arylboronic acids in DMSO. The prepared catalyst was characterized by FT-IR, XRD, SEM, EDX, BET, BJH and ICP-AES analysis. [CuBpm·2H2O]n as catalyst demonstrated good to excellent yields for Suzuki reaction in comparison with other catalysts. The catalyst was recovered by a simple filtration and retained its activity even after several cycles.
Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction
?zdemir, ?smail,Akko?, Mitat,Alt?n, Serdar,Bu?day, Nesrin,Ya?ar, Sedat
, (2021/08/03)
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.]
Magnetite@MCM-41 nanoparticles as support material for Pd-N-heterocyclic carbene complex: A magnetically separable catalyst for Suzuki–Miyaura reaction
Akko?, Mitat,Bu?day, Nesrin,Alt?n, Serdar,Ya?ar, Sedat
, (2021/03/22)
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
Akko?, Mitat,Bu?day, Nesrin,Alt?n, Serdar,Kiraz, Nadir,Ya?ar, Sedat,?zdemir, ?smail
, (2021/05/05)
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.
Pd-NHCs Enabled Suzuki-Miyaura Cross-Coupling of Arylhydrazines via C–N Bond Cleavage
Zeng, Xiao-Xiao,Li, Dong-Hui,Zhou, Zhen,Xu, Chang,Liu, Feng-Shou
supporting information, (2021/03/01)
We describe a highly efficient protocol for cross-coupling of phenylhydrazines with arylboronic acids by Pd-NHCs under aerobic reaction condition. A series of well-defined Pd-NHCs complexes were evaluated and the relationship between the structure and the catalytic properties was investigated. It was disclosed that the Pd-PEPPSI-IPr proved to be the robust precatalyst, providing access to a range of (hetero)biaryls in good to excellent yields.
Copper catalysed Gomberg-Bachmann-Hey reactions of arenediazonium tetrafluoroborates and heteroarenediazonium o-benzenedisulfonimides. Synthetic and mechanistic aspects
Antenucci, Achille,Barbero, Margherita,Dughera, Stefano,Ghigo, Giovanni
, (2020/10/20)
Gomberg-Bachmann-Hey reactions were carried out in the presence of copper as a catalyst and gave rise to biaryls or heterobiaryls in good yields and in mild reaction conditions. A computational study of some key points of the reaction was performed. The results are coherent with the experimental data and confirm some aspects of the mechanism. The reaction free energies for the reduction in benzene by CuI of a set of 40 (hetero)arenediazonium tetrafluoroborates were calculated. Both the experiments and the calculations showed that in the coupling with substituted solvents (toluene, bromobenzene, nitrobenzene and anisole) the binding to the ortho position was always favoured.
Synthesis and characterization of Pd based on [2,2'- bipyridin]-4-amine functionalized nano cellulose as a novel and recyclable nano catalyst for Suzuki reaction
Mohammadnia, Majid,Sun, Yuqi
, (2020/06/29)
In this work, it was designed and prepared an efficient nanocatalyst Pd based on [2,2'- bipyridin]-4-amine functionalized nano cellulose (Pd?BPA?CNC) and then characterized by FT-IR, XRD, ICP-AES, EDX, SEM, TEM and TGA techniques. The catalytic activity of the nanocatalyst was investigated through one-pot synthesis of biaryl derivatives from the reaction of aryl halides with arylboronic acids in DMSO solvent conditions. This Simple and mild procedure displayed excellent recyclability and provided cleaner conversion in a short reaction time. All of these advantages make the protocol feasible and economical attractive for researchers.
N-Heterocarbene Palladium Complexes with Dianisole Backbones: Synthesis, Structure, and Catalysis
Li, Dong-Hui,He, Xu-Xian,Xu, Chang,Huang, Fei-Dong,Liu, Ning,Shen, Dong-Sheng,Liu, Feng-Shou
, p. 2539 - 2552 (2019/06/17)
A series of palladium N-heterocyclic carbenes (NHCs), complexes C1-C5, bearing dianisole backbones and substituted N-aryl moieties have been synthesized and characterized. The electronic effect as well as the steric environment of the NHC ligands has been assessed. The synthesized palladium complexes were applied for Suzuki-Miyaura cross-coupling reactions under aerobic conditions. The relationship between the catalytic structure and catalytic performance was then extensively investigated. Upon optimizing the reaction conditions, the C4 was found to be highly efficient to catalyze the cross-coupling of (hetero)aryl chlorides with (hetero)arylboronic acids at a 0.1 mol % palladium loading.
