605-02-7Relevant articles and documents
Palladium-catalyzed coupling of aryl halides with arylhalosilanes in air and water
Huang, Taisheng,Li, Chao-Jun
, p. 403 - 405 (2002)
In the presence of a palladium catalyst, various aryl halides reacted with arylhalosilanes in aqueous media and under an air atmosphere to give the corresponding unsymmetrical aryl-aryl coupling products conveniently.
A highly acid labile silicon linker for solid phase synthesis
Hone, Neal D.,Davies, Stephen G.,Devereux, Nicholas J.,Taylor, Sara L.,Baxter, Anthony D.
, p. 897 - 900 (1998)
A novel arylsilane based linker has been prepared for the solid phase synthesis of small molecule combinatorial libraries. Efficient cleavage is achieved using TFA via anchimerically assisted protiodesilylation to yield aromatic products possessing no residual linker functionality.
One-pot Solvent-free Catalytic Dimerization Reaction of Phenylacetylene to 1-Phenylnaphthalene
Taherpour, Avat,Taban, Sepehr,Yari, Ako
, p. 1523 - 1530 (2015)
In this study, we report a smooth one-pot, solvent-free catalytic dimerization of phenylacetylene (1) to 1-phenylnaphthalene (2) by Cu/C at room temperature in good yield (～100%). In the computational study, the structure of the 1-phenylnaphthalene was optimized by DFT-B3LYP/6-31Gmethod. The rotation barrier around C-C of the phenyl and naphthalene parts of the molecule and its UV-Visible spectrum were calculated. The modelling of the mechanism of production of 2 from 1 was performed with and without Cu/C catalyst. The data of EDS and SEM of the Cu/C catalyst surface are also reported.
Confinement effects at the external surface of delaminated zeolites (ITQ-2): An inorganic mimic of cyclodextrins
Galletero, Mariì?a S.,Corma, Avelino,Ferrer, Beleì?n,Forneì?s, Vicente,Garciì?a, Hermenegildo
, p. 1135 - 1141 (2003)
Novel delaminated ITQ-2 zeolite has a remarkably large accessible external surface area (a??800 m2 g-1) and reduced microporosity (0.009 cm-3 g-1) and has attracted interest as an alternative to conventional zeolites or mesoporous MCM-41 (Corma, A.; Forneì?s, V.; Pergher, S. B.; Maesen, T. L. M.; Buglass, J. G. Nature 1998, 396, 353-356). ?±,??-Diphenyl polyenes have been used as molecular probes to check the ability of ITQ-2 zeolite to generate organic radical cations. Of these probes, only t,t-1,4-diphenyl-1,3-butadiene (DPB) is transformed into a persistent reaction intermediate upon adsorption on ITQ-2. The process occurs in the cup -like cavities open to the exterior since selective silylation of the cups inhibits completely the generation of this reaction intermediate. Detection of 1-phenylnaphthalene as reaction product, EPR spectroscopy, and alternative laser flash photolysis generation strongly support 1-phenylnaphthalene radical cation as the intermediate formed after the adsorption of DPB onto ITQ-2. This contrasts with the behavior of conventional zeolites ZSM-5 and mordenite in which DPBì?+ is the only species formed and demonstrates the uniqueness of the behavior of ITQ-2 as result of its unprecedented topology.
Solid-supported palladium nano and microparticles: An efficient heterogeneous catalyst for ligand-free Suzuki-Miyaura cross coupling reaction
Das, Pralay,Sharma, Dharminder,Shil, Arun K.,Kumari, Avnesh
, p. 1176 - 1178 (2011)
Solid-supported nano and microparticles of Pd(0) (SS-Pd) were prepared and used as a heterogeneous catalysts for Suzuki-Miyaura cross coupling reactions of aryl halides (chloro, bromo and iodo) and phenyl boronic acid under mild and ligand-free conditions. Scanning electron microscope (SEM) and UV-vis based studies were performed to observe the distribution of nano and microparticles of palladium over solid surface and their oxidation states. In addition, the catalyst could be reused up to seven runs without significant loss of activity and stable enough under moist conditions.
Pd(II)-catalyzed synthesis of unsymmetrical biaryls from tetraphenylborate and aryl halides under microwave activation
Wang, Jin-Xian,Yang, Yihua,Wei, Bangguo
, p. 2063 - 2069 (2004)
A rapid and efficient method for synthesis of unsymmetrical biaryls under microwave irradiation conditions is described. The process involves the reactions of sodium tetraphenylborate with aryl halides in the presence of catalytic amount [PdCl2(PPh3)2] with KF/Al 2O3 under microwave irradiation to afford the unsymmetrical biaryls in good to excellent isolated yields.
Deposited zirconocene chloride on silica-layered CuFe2O4 as a highly efficient and reusable magnetically nanocatalyst for one-pot Suzuki-Miyaura coupling reaction
Zeynizadeh, Behzad,Sepehraddin, Farhad
, p. 70 - 77 (2018)
The novel core-shell magnetically nanoparticles of CuFe2O4@SiO2@ZrCp2Clx (x: 0–2) were synthesized and used as a highly efficient catalyst for Suzuki-Miyaura coupling reaction of various aryl halides with phenylboronic acid. The reactions were carried out in PEG-400 (70 °C) to afford biaryls in high to excellent yields. The core-shell nanocomposite was easily separated from the reaction by an external magnet and reused for 5 times without significant loss of its catalytic activity. Characterization of the zirconocene nanocomposite was carried out by FT-IR, SEM, EDX, XRD, ICP-OES, AGFM, TGA and BET analyses.
Heterogeneous Suzuki reactions catalyzed by Pd(0)-Y zeolite
Artok, Levent,Bulut, Hatice
, p. 3881 - 3884 (2004)
The Pd(0)-Y zeolite showed high activity in the Suzuki cross-coupling reactions of aryl bromides without added ligands. The type of base and organic solvent were found to be critical for the efficiency of the reaction. The presence of water was essential within the reaction medium. The coupling reactions occurred on the external surface of the zeolite. The catalyst is reusable.
Combination of polymer and halloysite chemistry for development of a novel catalytic hybrid system
Sadjadi, Samahe,Malmir, Masoumeh,Pourmohammad, Nargess,Ahmadi, Shervin,Heravi, Majid M.
, p. 4349 - 4366 (2019)
Abstract: A covalent hybrid of halloysite-poly(methyl methacrylate-co-maleic anhydride) was prepared and applied for the immobilization of Pd nanoparticles. The hybrid system, Pd@Hal-Gua-Poly, was then characterized via TEM, TGA, ICP, BET, FTIR and XRD and successfully used as a heterogeneous catalyst for promoting two main Pd-catalyzed reactions, i.e. hydrogenation of nitro-arenes and Suzuki coupling reaction under mild and eco-friendly conditions. The study of recyclability of the catalyst confirmed high recyclability and low Pd leaching of Pd@Hal-Gua-Poly. Moreover, the hot-filtration test showed the heterogeneous nature of the catalysts. Notably, the comparison of the activity of the catalyst with that of Pd@Hal and Pd@Poly confirmed the superior catalytic activity of the former, indicating that the hybridization of Hal and Poly could lead to the improvement of the catalytic activity. Graphical abstract: [Figure not available: see fulltext.].
Highly dispersed palladium(II) in a defective metal-organic framework: Application to C-H activation and functionalization
Park, Tae-Hong,Hickman, Amanda J.,Koh, Kyoungmoo,Martin, Stephen,Wong-Foy, Antek G.,Sanford, Melanie S.,Matzger, Adam J.
, p. 20138 - 20141 (2011)
High reversibility during crystallization leads to relatively defect-free crystals through repair of nonperiodic inclusions, including those derived from impurities. Microporous coordination polymers (MCPs) can achieve a high level of crystallinity through a related mechanism whereby coordination defects are repaired, leading to single crystals. In this work, we discovered and exploited the fact that this process is far from perfect for MCPs and that a minority ligand that is coordinatively identical to but distinct in shape from the majority linker can be inserted into the framework, resulting in defects. The reaction of Zn(II) with 1,4-benzenedicarboxylic acid (H2BDC) in the presence of small amounts of 1,3,5-tris(4-carboxyphenyl)benzene (H 3BTB) leads to a new crystalline material, MOF-5(Oh), that is nearly identical to MOF-5 but has an octahedral morphology and a number of defect sites that are uniquely functionalized with dangling carboxylates. The reaction with Pd(OAc)2 impregnates the metal ions, creating a heterogeneous catalyst with ultrahigh surface area. The Pd(II)-catalyzed phenylation of naphthalene within Pd-impregnated MOF-5(Oh) demonstrates the potential utility of an MCP framework for modulating the reactivity and selectivity of such transformations. Furthermore, this novel synthetic approach can be applied to different MCPs and will provide scaffolds functionalized with catalytically active metal species.
