2143-88-6Relevant articles and documents
A palladium-loaded mesoporous polymer monolith as reusable heterogeneous catalyst for cross-coupling reactions
Kundu, Dhiman,Patra, Astam K.,Sakamoto, Junji,Uyama, Hiroshi
, p. 8 - 13 (2014)
A new palladium catalyst based on a mesoporous polymer monolith has been introduced. A polyacrylonitrile (PAN) monolith prepared by a phase separation technique was used as precursor material for chemical modification; the nitrile groups on the monolith surface were transformed into amidine groups and then bound to palladium dichloride via coordination. A series of Suzuki-Miyaura cross-coupling reactions were successfully demonstrated by using the monolith as catalyst. Moreover, the monolith was found to exhibit excellent stability for repeated use.
Highly active, durable and recyclable ordered mesoporous magnetic organometallic catalysts for promoting organic reactions in water
Zhang, Fang,Chen, Mingzhen,Wu, Xiaotao,Wang, Wei,Li, Hexing
, p. 484 - 491 (2014)
A new strategy of bonding organometallics to an MCM-41 thin layer coated onto Fe3O4 microspheres with strong magnetism, denoted as M-PPh2-MCM-41@SiO2@Fe3O4, where M = Pd(ii) and Rh(i), has been developed for the immobilization of homogeneous catalysts. In comparison with the traditional M-PPh2-MCM-41 catalysts with irregular shapes and the M-PPh2-SiO2@Fe 3O4 without an ordered mesoporous structure, the current catalysts exhibited much higher activities for various water-based Suzuki, Sonogashira and Miyaura-Michael organic reactions, due to the high dispersion of active sites and the uniform catalyst particles with short-ordered mesopores favoring reactant diffusion and adsorption. Their catalytic efficiencies are comparable with those of the homogeneous catalysts, and they could be easily recycled for reuse by simply applying an external magnet.
Stille-type aryl-aryl cross-coupling catalysis using triarylphosphine ligands with electron-rich Fe(ii)-alkynyl substituents
Grelaud, Guillaume,Tohme, Ayham,Argouarch, Gilles,Roisnel, Thierry,Paul, Frederic
, p. 2740 - 2742 (2011)
The synthesis of four new phosphane ligands featuring electron-rich Fe(ii) "(η2-dppe)(η5-C5Me 5)FeCC-" substituents in para and meta position(s) on the aryl rings (1-4) is reported along with those of the corresponding PdCl 2(PAr3)2 precatalysts (7-10). These precatalysts have then been tested in a Stille-type aryl-aryl cross coupling reaction. It is shown that these new ligands survive the reaction conditions and perform at least as well as the classic triphenylphosphine ligand for this transformation.
Studies on the catalytic ability of palladium wire, foil and sponge in the Suzuki-Miyaura cross-coupling
Amoroso, Francesco,Cersosimo, Ulma,Del Zotto, Alessandro
, p. 256 - 262 (2011)
Different forms of metallic palladium (wire, foil and sponge) have been tested as potential catalysts in the Suzuki-Miyaura cross-coupling. All samples showed to be catalytically active for both electron-poor and electron-rich aryl bromides combined with a variety of arylboronic acids. Palladium wire has been recycled six times without decrease of activity. A series of poisoning experiments demonstrated that the true catalyst is a soluble form of palladium arising from a leaching process. Interestingly, metal leaching from palladium foil has been clearly evidenced by SEM.
Enhancing activity of Suzuki reactions in water by using guanidinium ionic liquid stabilized palladium micelle catalyst
Lin, Li,Li, Yanchun,Zhang, Suobo,Li, Shenghai
, p. 1779 - 1783 (2011)
A facile surfactant-based hexaalkylguanidinium ionic liquid (GIL)-mediated Suzuki coupling procedure has been developed using ligand-free Pd catalysts. The procedure involving the use of nanometric palladium micelles, is operationally simple and remarkably efficient for the coupling of aryl bromides or aryl chlorides with boronic acids in water. Furthermore, the GIL/H2O catalytic system was more stable than the tetrabutylammonium bromide/H 2O catalytic system under basic conditions, enabling the recycling of the nano-Pd micelle catalysts. Georg Thieme Verlag Stuttgart · New York.
Synthesis and catalytic activity of cationic dinuclear palladium (II) complexes supported by thioether ligands containing two di-(2-picolyl) amine arms
Andrade-López, Noemi,González-Montiel, Simplicio,Martínez-Otero, Diego,Salazar-Pereda, Verónica,Sandoval-Chávez, César Ignacio,Velázquez-Jiménez, René
, (2020)
The design, synthesis and characterization of a series of dithioether ligands featuring two di-(2-picolyl)amine arms (2a–2d) and their corresponding cationic dinuclear palladium (II) complexes (3a–d) are reported. Crystal structures of ligand 2b and complexes 3b and 3d were determined by X-ray diffraction studies. The molecular structures of 3b and 3d display each of the two di-(2-picolyl)amine fragments coordinated to one palladium(II) atom in a (κ3-N,N,N) tridentate fashion and with the cationic metal centers displaying square-planar geometries. Weak interactions between the metal centers and the thioether fragments are observed. All bimetallic complexes 3a–d were tested as catalytic precursors in the Suzuki couplings of different o- or p-substituted iodo- or bromoaryls with boronic acids. The overall catalytic results indicate that complex 3b is the best precursor of the series demonstrating even more efficient performance compared to commercial palladium sources such as Pd(OAc)2 and the Nájera Catalysts.
Ionic-liquid-grafted rigid poly (p-Phenylene) microspheres: Efficient heterogeneous media for metal scavenging and catalysis
Li, Shenghai,Wang, Junhua,Kou, Yongli,Zhang, Suobo
, p. 1812 - 1818 (2010)
Novel guanidinium ionic liquid-grafted rigid poly(p-phenylene) (PPPIL) microspheres have been developed for metal scavenging and catalysis. The noble-metal nanoparticles supported on the microspheres surface can be used as efficient heterogeneous catalysts. The combination of nanoparticles and ionic liquid fragments on the microsphere surfaces enhance the activity and durability of the catalyst. The PPPIL-Pd0 catalyst has been tested in the Suzuki cross-coupling reaction, and exhibits much higher catalytic activity than Pd catalysts supported on porous polymer matrices. The PPPIL-Pd0 catalyst can be recycled at least for nine runs without any significant loss of activity. The present approach may, therefore, have potential applications in transition-metal-nanocatalyzed reactions.
Improving the rates of Pd-catalyzed reactions by exciting the surface plasmons of AuPd bimetallic nanotriangles
Gangishetty, Mahesh K.,Fontes, Adriana M.,Malta, Marcos,Kelly, Timothy L.,Scott, Robert W.J.
, p. 40218 - 40226 (2017)
Gold nanoparticles exhibit unique optical properties due to surface plasmon oscillations when they interact with light. By utilizing their optical properties, the rates of many chemical reactions have been improved in the presence of visible light. The properties of plasmonic nanoparticles are highly tunable based on the size and shape of the nanoparticle. Here, we have used anisotropic AuPd bimetallic nanotriangles to improve the rates of Pd-catalyzed reactions in the presence of visible light. We synthesized AuPd core-shell bimetallic nanotriangles and performed Suzuki cross-coupling and hydrogenation reactions in light and dark conditions. Upon illuminating AuPd nanotriangles with an array of green LEDs (power ～ 500 mW), enhanced catalytic activity of palladium was observed. In order to understand the relative contributions of individual plasmonic effects, such as plasmonic hot electron transfer and plasmonic heating effects, the reaction temperatures were monitored, and careful control experiments were run at different temperatures. Our results indicated that the enhancement in the rate of these Pd-catalyzed reactions is primarily due to the plasmonic heating effect.
Suzuki-Miyaura reactions of aryl chloride derivatives with arylboronic acids using mesoporous silica-supported aryldicyclohexylphosphine
Sayah, Reine,Glegola, Katarzyna,Framery, Eric,Dufaud, Veronique
, p. 373 - 381 (2007)
The Suzuki-Miyaura reactions using mesoporous-supported aryldicyclohexylphosphine as ligand have been investigated. The catalysts were based on SBA-15 type mesoporous silica which was transformed in a four-step synthesis leading to a phosphine-containing hybrid material The most productive catalytic system studied was generated in situ from this material and the homogeneous palladium complex, Pd(OAc)2. Other catalytic systems were studied for comparison [homogeneous cataysts, a "preformed" catalyst obtained by reaction of PdCl2 (PhCN)2 and the phosphine-containing material]. Variations involving the solvent system, the substrate aryl chloride and the arylboronic acid reactant were also studied. For both in situ and preformed cataiyst systems, high conversions and yields are obtained for activated aryl chlorides. Success of the reaction for unactivated aryl chlorides was limited to the catalyst formed in situ. The catalyst formed in situ was also shown to be reactive under aqueous reaction conditions in the cross-coupling of 1-(4-chlorophenyl)ethanone with phenylboronic acid.
Simple mixed tricyclohexylphosphane-triarylphosphite complexes as extremely high-activity catalysts for the Suzuki coupling of aryl chlorides
Bedford, Robin B.,Cazin, Catherine S. J.,Hazelwood, Samantha L.
, p. 4120 - 4122 (2002)
The most active catalyst yet reported for the Suzuki coupling of activated aryl chlorides, even for electronically deactivated substrates, is generated by addition of tricyclohexylphosphane to the otherwise inactive orthopalladated complex 1 [Eq. (1); for
Palladium on carbon-catalyzed cross-coupling of aryl halides with potassium p-tolyltrifluoroborate in air
LeBlond, Carl R.,Butler, Kaycie M.,Ferrington, Marc W.,Browe, Matthew A.
, p. 636 - 640 (2009)
Palladium supported on carbon (Pd/C) has been shown to be an effective catalyst for the cross-coupling of potassium p-tolyltrifluoroborate with a variety of aryl bromides and iodides. Yields ranging from moderate to good were obtained using Pd/C in ethano
Anchoring of palladium (II) in functionalized SBA-16: An efficient heterogeneous catalyst for Suzuki coupling reaction
Wei, Shuoyun,Ma, Zongyan,Wang, Peng,Dong, Zhengping,Ma, Jiantai
, p. 175 - 181 (2013)
A new functionalized SBA-16 catalyst immobilized palladium (II) has been synthesized. Inductively coupled plasma (ICP), small-angle X-ray diffraction (XRD), transmission electron microscopy (TEM), nitrogen physical adsorption and Fourier transform infrared (FTIR) studies have been used to characterize the catalyst. The catalyst exhibited very high activity for Suzuki coupling reaction of aryl halides with arylboronic acids in EtOH/water under air atmosphere. On the other hand, the synthesized catalyst could be separated from the reaction mixture by simple filtration and reused up to five runs without significant loss in activity.
Suzuki-Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst
Kawase, Misa,Matsuoka, Kyosuke,Shinagawa, Tsutomu,Hamasaka, Go,Uozumi, Yasuhiro,Shimomura, Osamu,Ohtaka, Atsushi
, p. 57 - 61 (2021/11/13)
This paper describes the Suzuki Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PSPdONPs). The reaction of aryl bromides having electron-withdrawing groups or electron-donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of PdNPs was observed after the reaction.
Palladium-catalyzed aryl group transfer from triarylphosphines to arylboronic acids
Enright, Dale R.,Gogate, Akash R.,Smoliakova, Irina P.,Vasireddy, Purna C. R.
, (2021/11/11)
A study of Pd-catalyzed arylation of arylboronic acids with triarylphosphines is presented. Various parameters of this transformation, such as the oxygen presence, choice of solvent, temperature, palladium source, bases and oxidants, were tested and the optimal conditions of the aryl transfer were determined. The effect of electron-withdrawing and electron-donating substituents on the aryl groups of both reactants was also investigated. The unusual transfer of the acetate group from Pd(OAc)2 to p-nitrophenylboronic acid in the presence of PAr3 is reported. A plausible mechanism of the Pd-catalyzed aryl group transfer from PAr3 to the arylboronic acid is proposed.
