37847-52-2Relevant articles and documents
Pd nanoparticles in silica hollow spheres with mesoporous walls: A nanoreactor with extremely high activity
Chen, Zhe,Cui, Zhi-Min,Niu, Fang,Jiang, Lei,Song, Wei-Guo
, p. 6524 - 6526 (2010)
A true nanoreactor composed of mesoporous silica hollow spheres and Pd nanoparticles residing inside the spheres shows superior activity in Suzuki coupling reactions with 99.5% yield in 3 min.
Magnetic Nanoparticle-Supported N-Heterocyclic Carbene-Palladium(II): A Convenient, Efficient and Recyclable Catalyst for Suzuki–Miyaura Cross-Coupling Reactions
Vishal,Fahlman, Bradley D.,Sasidhar,Patil, Shivaputra A.,Patil, Siddappa A.
, p. 900 - 918 (2017)
Abstract: A new magnetic nanoparticle-supported N-heterocyclic carbene-palladium(II) nanomagnetic catalyst was synthesized and appropriately characterized using attenuated total reflectance infrared spectroscopy (ATR-IR), ultraviolet–visible spectroscopy (UV–Visible), inductively coupled plasma-atomic emission spectroscopy (ICP-AES), energy-dispersive X-ray spectroscopy (EDS), field-emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM), X-ray powder diffraction (XRD), thermogravimetric analysis (TGA) and Brunauer–Emmett–Teller surface area analysis (BET). The nanomagnetic catalyst was used as convenient and efficient catalyst for the Suzuki–Miyaura cross-coupling reaction of various aryl bromides/chlorides/iodide with phenylboronic acid. The effects of varying solvents, bases, temperature, time and catalytic ratios on the performance of the Suzuki–Miyaura cross-coupling reaction were investigated. The notable advantages of this heterogeneous nanomagnetic catalyst are excellent yields, mild reaction conditions, short reaction times and easy work-up. Moreover, the new nanomagnetic catalyst could be easily recovered with an external magnet and could be reused at least five times without loss of its catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]
An efficient heterogeneous Pd catalyst for the Suzuki coupling: Pd/Al 2O3
Kudo, Daisuke,Masui, Yoichi,Onaka, Makoto
, p. 918 - 919 (2007)
PdII-loading alumina catalyst, which is simply prepared through impregnation of γ-alumina with Pd(OAc)2 followed by calcination in the air, shows a high catalytic activity for the Suzuki coupling of aryl bromides with arylboronic acids under phosphine ligand-free conditions. Only 0.25 mol% of palladium is sufficient for the promotion of the couplings in ethanol. Copyright
Method for synthesizing biphenyl compounds by adopting microchannel reactor
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Paragraph 0045-0050, (2021/11/10)
The invention relates to a method for synthesizing biphenyl compounds by adopting a microchannel reactor. The method comprises the following steps: mixing a compound shown in a formula (1), a compound shown in a formula (2), a compound shown in a formula (3) and a copper catalyst in the microchannel reactor, carrying out diazotization coupling reaction, and purifying the obtained reaction product to obtain a compound shown in a formula (4). Compared with the prior art, the micro-channel reactor is adopted, so that the diazotization coupling reaction time is effectively shortened, the reaction stability and efficiency are improved, the reaction yield and purity are improved, and the method has the advantages of environmental protection, safety, simple process, low cost, continuous industrial production and the like.
Photoelectric properties of aromatic triangular tri-palladium complexes and their catalytic applications in the Suzuki-Miyaura coupling reaction
Li, Jia,Li, Xujun,Liu, Xiang,Maestri, Giovanni,Malacria, Max,Wang, Xiaoshuang,Wang, Yanlan,Wu, Lingang
supporting information, p. 11834 - 11842 (2021/09/06)
The photoelectric properties and catalytic activities of substituted triphenylphosphine and sulfur/selenium ligand supported aromatic triangular tri-palladium complexes1-4, abbreviated as [Pd3]+, were investigated. The cyclic voltammogram of [Pd3]+in CH3CN-nBu4NPF6showed a single quasi-reversible wave which was consistent with their robust property and provided preliminary proof for their electron transfer processes in catalysis. With excitation at 267 nm, [Pd3]+exhibited strong ratiometric fluorescence at 550 and 780 nm at a temperature gradient from 77 K to 287 K. These peculiar triangular tri-palladium complexes showed excellent catalytic activities and exclusive reactivity with aryl iodides over the other halogenated aromatics in the Suzuki-Miyaura coupling reaction. The electronic and steric hindrance effects of substituents on the aryl iodides and aryl boronic acids including heteroaromatics like pyridine, pyrazine and thiophenes were explored and most substrates achieved up to 99% of yields. (2-[1,1′-Biphenyl]-2-ylbenzothiazole) which was analogous to the selective cyclooxygenase-2 (COX-2) inhibitors was also synthesized with our tri-palladium catalyst and gave good isolated yield (94%). The study of the catalytic process revealed that the mechanism of the reaction may involve the replacement of the sulphur ligand on [Pd3]+by iodine from aryl iodides, which was beneficial for the matching of C-I bond energy.
Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance
Bunda, Szilvia,Joó, Ferenc,Kathó, ágnes,Udvardy, Antal,Voronova, Krisztina
supporting information, (2020/09/18)
Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2?. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved highly active catalysts of the Suzuki–Miyaura reaction of aryl halides and arylboronic acid derivatives at 80 ?C in water and air. A comparative study of the Pd (II)–sulfosalan catalysts showed that the catalytic activity largely increased with increasing linker length and with increasing steric congestion around the N donor atoms of the ligands; the highest specific activity was 40,000 (mol substrate) (mol catalyst × h)?1. The substrate scope was explored with the use of the two most active catalysts, containing 1,4-butylene and 1,2-diphenylethylene linkers, respectively.
Recombinant Peptide Fusion Protein-Templated Palladium Nanoparticles for Suzuki-Miyaura and Stille Coupling Reactions
Mosleh, Imann,Shahsavari, Hamid R.,Beitle, Robert,Beyzavi, M. Hassan
, p. 2942 - 2946 (2020/03/26)
This study examined the use of nanoparticles created with recombinant 45-amino acid long peptides fused to green fluorescent protein (GFPuv) to catalyze twelve representative Suzuki-Miyaura and Stille coupling reactions. A method was developed to prepare powders (Pd@GFP) containing protein and synthesized nanoparticles. Next, coupling reactions were performed in a green solvent without nanoparticle purification. Pd@GFP had high turnover frequencies for the synthesis of model compounds including lapatinib (Tykerb) and could be recycled. This study establishes a potentially cost-effective approach to prepare heterogeneous catalysts containing well-defined nanoparticles enabling key C?C bond formation leading to synthetically and pharmaceutically interesting compounds.
Magnetite tethered mesoionic carbene-palladium (II): An efficient and reusable nanomagnetic catalyst for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions in aqueous medium
Kempasiddhaiah, Manjunatha,Kandathil, Vishal,Dateer, Ramesh B.,Sasidhar, Balappa S.,Patil, Shivaputra A.,Patil, Siddappa A.
, (2019/03/07)
In this paper, a highly active, air- and moisture-stable and easily recoverable magnetic nanoparticles tethered mesoionic carbene palladium (II) complex (MNPs-MIC-Pd) as nanomagnetic catalyst was successfully synthesized by a simplistic multistep synthesis under aerobic conditions using commercially available inexpensive chemicals for the first time. The synthesized MNPs-MIC-Pd nanomagnetic catalyst was in-depth characterized by numerous physicochemical techniques such as FT-IR, ICP-AES, FESEM, EDS, TEM, p-XRD, XPS, TGA and BET surface area analysis. The prepared MNPs-MIC-Pd nanomagnetic catalyst was used to catalyze the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions and exhibited excellent catalytic activity for various substrates under mild reaction conditions. Moreover, MNPs-MIC-Pd nanomagnetic catalyst could be easily and rapidly recovered by applying an external magnet. The recovered MNPs-MIC-Pd nanomagnetic catalyst exhibited very good catalytic activity up to ten times in Suzuki–Miyaura and five times in Mizoroki–Heck cross-coupling reactions without considerable loss of its catalytic activity. However, MNPs-MIC-Pd nanomagnetic catalyst shows notable advantages such as heterogeneous nature, efficient catalytic activity, mild reaction conditions, easy magnetic work up and recyclability.
From agriculture residue to catalyst support; A green and sustainable cellulose-based dip catalyst for C–C coupling and direct arylation
Kandathil, Vishal,Kempasiddaiah, Manjunatha,B. S., Sasidhar,Patil, Siddappa A.
, (2019/07/31)
The core characteristics of a perfect catalyst include good activity, simple design, excellent stability, easy recovery from reaction mixture, recyclability, and have the provision for easy scale up. The ease in synthesis, recyclability and scale up makes the dip catalyst a major contender in this regard which possess most of the aforementioned characteristics. In this work, we report a dip catalyst made of cellulose, isolated from agriculture residue (sugarcane bagasse), in which biogenically synthesized palladium nanoparticles were dispersed. The prepared dip catalyst was characterized by FESEM, EDS, XRD, ATR-IR, TGA, TEM, XPS and ICP-OES analysis. Also, the activity of the dip catalyst was studied in the Suzuki-Miyaura cross-coupling reaction and was found to give excellent conversion with 15 recycles. Further, the activity of dip catalyst in C5-arylation of 2-substituted thiophenes was evaluated for which promising yields were obtained.
Catalytic reduction of aryl trialkylammonium salts to aryl silanes and arenes
Rand, Alexander W.,Montgomery, John
, p. 5338 - 5344 (2019/05/29)
A new approach for the reduction of aryl ammonium salts to arenes or aryl silanes using nickel catalysis is reported. This method displays excellent ligand-controlled selectivity based on the N-heterocyclic carbene (NHC) ligand employed. Utilizing a large NHC in non-polar solvents generates aryl silanes, while small NHCs in polar solvents promote reduction to arenes. Several classes of aryl silanes can be accessed from simple aniline building blocks, including those useful for cross-couplings, oxidations, and halogenations. The reaction conditions are mild, functional group tolerant, and provide efficient access to a variety of benzene derivatives.
