643-93-6Relevant articles and documents
Suzuki-Miyaura Cross-Coupling Using Plasmonic Pd-Decorated Au Nanorods as Catalyst: A Study on the Contribution of Laser Illumination
Verkaaik, Mattheus,Grote, Roos,Meulendijks, Nicole,Sastre, Francesc,Weckhuysen, Bert M.,Buskens, Pascal
, p. 4974 - 4980 (2019)
The interaction between plasmonic metal catalysts and visible light can be exploited to increase their catalytic activity. This activity increase results from the generation of hot charge carriers or hot surfaces, or a combination of both. We have studied the light-induced Suzuki-Miyaura cross-coupling reaction of bromobenzene and m-tolylboronic acid using Pd-decorated Au nanorods as plasmonic catalyst in order to assess which physical effect dominates. Comparative experiments under laser illumination and in dark were performed, demonstrating that under the experimental conditions applied in our study the catalytic activity achieved upon illumination is dominantly based on the conversion of light to heat by the plasmonic catalyst. Pd leached from the catalyst also plays a significant role in the reaction mechanism.
Novel imidazolium and imidazolinium salts containing the 9-nickelafluorenyl anion - Synthesis, structures and reactivity
Buchalski, Piotr,Pacholski, Roman,Chodkiewicz, Krzysztof,Buchowicz, W?odzimierz,Suwińska, Kinga,Shkurenko, Aleksander
, p. 7169 - 7176 (2015)
Investigation of the properties of carbene complexes is one of the most important fields of modern coordination chemistry. In this paper, we propose the convenient synthesis of NHC-nickel compounds. The 9-nickelafluorenyllithium complex reacts with imidazolium or imidazolinium salts to afford 9-nickelafluorenyl-NHC salts via ionic metathesis with very good yields (66-92%). These compounds can be isomerised at elevated temperatures to give Ni-NHC complexes with excellent yields (88-91%), probably via nickel mediated hydrogen transfer to the biphenyl moiety. In this reaction, the nickelacyclic ring itself serves as a base in the deprotonation of the carbene precursor. DFT calculations show the thermodynamic instability of the synthesized salts, with Gibbs free energy differences for 1 of -84 kJ mol-1 at 298 K and -167 kJ mol-1 at 374 K. The obtained salts and carbene complexes are relatively air and moisture stable in the solid state.
A novel fluorous palladium catalyst for Suzuki reaction in fluorous media
Shen, Ming-Gui,Cai, Chun,Yi, Wen-Bin
, p. 1421 - 1424 (2007)
Palladium(II) perfluorooctanesulfonate [Pd(OSO2Rf8)2] catalyses the highly efficient Suzuki reaction in the presence of a catalytic amount of perfluoroalkylated-pyridine as a ligand in a fluorous biphase system (FBS). The fluorous phase containing the active palladium species is easily separated and can be reused several times without a significant loss of catalytic activity.
Nickel(II) complexes of bidentate N-heterocyclic carbene/phosphine ligands: Efficient catalysts for suzuki coupling of aryl chlorides
Lee, Chun-Chin,Ke, Wei-Chi,Chan, Kai-Ting,Lai, Chun-Liang,Hu, Ching-Han,Lee, Hon Man
, p. 582 - 591 (2007)
Nickel(II) complexes of bidentate N-heterocyclic carbene (NHC)/phosphane ligand L were prepared and structurally characterized. Unlike palladium, which forms [PdCl2(L)], the stable nickel product isolated is the ionic [Ni(L)2]Cl2. These NiII complexes are highly robust in air. Among different N-substituents on the ligand framework, the nickel complex of ligand L bearing N-1-naphthylmethyl groups (2 a) is a highly effective catalyst for Suzuki cross-coupling between phenylboronic acid and a range of aryl halides, including unreactive aryl chlorides. The activities of 2a are largely superior to those of other reported nickel NHC complexes and their palladium counterparts. Unlike the previously reported [NiCl2(dppe)] (dppe = 1,2-bis(diphenylphosphino)ethane), 2a can effectively catalyze the cross-coupling reaction without the need for a catalytic amount of PPh 3, and this suggests that the PPh2 functionality of hybrid NHC ligand L can partially take on the role of free PPh3. However, for unreactive aryl chlorides at low catalyst loading, the presence of PPh 3, accelerates the reaction.
Magnetic Mesoporous Silica Nanocomposite Functionalized with Palladium Schiff Base Complex: Synthesis, Characterization, Catalytic Efficacy in the Suzuki–Miyaura Reaction and α-Amylase Immobilization
Ahmadi, Ameneh,Sedaghat, Tahereh,Azadi, Roya,Motamedi, Hossein
, p. 112 - 126 (2020)
Abstract: Magnetic mesoporous silica nanocomposite, Fe3O4-MCM-41, was functionalized with N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAPS) and then condensed with 5,5′-methylene bis(salicylaldehyde), followed by N(4)-phenylthiosemicarbazide to produce a ONS Schiff base grafted nanocomposite. Finally, by adding palladium(II) acetate, the palladium Schiff base complex was immobilized on magnetic nanocomposite. The characterization of new nanocomposites was carried out by means of several techniques such as FT-IR, XRD, FE-SEM, HRTEM, EDS, BET, VSM, XPS, DRS and TGA. The new nanocatalyst, Fe3O4@MCM-41-SB-Pd, was used in synthesis of symmetrical and unsymmetrical biaryl compounds via the Suzuki–Miyaura cross-coupling of phenylboronic acid with aryl halides. This catalyst was easily recovered by applying an external magnetic field and reused for several times without significant loss of its catalytic activity. Also the ability of synthesized mesoporous nanocomposites for enzyme immobilization was investigated and results showed that they efficiently immobilized α-amylase enzyme. Graphic Abstract: [Figure not available: see fulltext.].
Resin encapsulated palladium nanoparticles: An efficient and robust catalyst for microwave enhanced Suzuki-Miyaura coupling
Kaur, Harjinder,Shah, Dipen,Pal, Usha
, p. 1384 - 1388 (2011)
A simple and rapid method for synthesizing highly accessible supported palladium nanoparticles inside the matrix of a commercial resin is reported. The encapsulated palladium nanoparticles were observed by TEM. The prepared catalyst has shown very high tu
N-heterocyclic carbene conjugated with poly(ethylene glycol) for palladium-catalyzed Suzuki-Miyaura coupling in aqueous solvents
Shi, Ji-Cheng,Yu, Hongwei,Jiang, Dahong,Yu, Mei,Huang, Yanxian,Nong, Lanping,Zhang, Qing,Jin, Zilin
, p. 158 - 164 (2014)
Here we report a type of N-heterocyclic carbene (NHC)- and phosphine-chelated palladium catalysts with poly(ethylene glycol) (PEG) chain for Suzuki-Miyaura crosscoupling reactions. 1-(2-Diphenylphosphinoferrocenyl)- ethyl- 3-imidazolium iodides conjugated with MeO-PEG400 and MeO-PEG750, respectively, have been synthesized and characterized. It was demonstrated that the salts bearing with PEG chain could act as NHC precursors successfully under the catalytic condition to form NHC-supported palladium complexes joined by phosphine. The formed palladium complexes are highly efficient for Suzuki-Miyaura coupling of aryl bromides with phenylboronic acid at the palladium loading of 0.1 mol% in both organic and aqueous solvents.
Hollow porous organic nanospheres for anchoring Pd(PPh3)4 through a co-hyper-crosslinking mediated self-assembly strategy
Gao, Shengguang,Huang, Kun,Liu, Ying,Shi, Buyin,Yu, Haitao,Zhang, Li
, p. 6661 - 6666 (2020)
In this work, we present a facile method for anchoring a transition metal catalyst (Pd(PPh3)4) into hollow porous organic nanospheres (H-PONs) based on a co-hyper-crosslinking mediated self-assembly strategy by using polylactide-b-polystyrene (PLA-b-PS) and Pd(PPh3)4 as precursors. The intrinsic catalytic activity of Pd(PPh3)4 could be well retained even if immobilized into H-PONs through a one-step Scholl reaction. Owing to the hierarchically porous structure, high surface area and well-dispersed active sites, the resulting H-PONs-Pd(PPh3)4 exhibited excellent catalytic activity, enhanced stability, and good recyclability for the Suzuki-Miyaura coupling in aqueous media. We hope that such a facile synthesis approach can provide a broad platform to support various transition metal catalysts anchored into hollow porous nanomaterials for the heterogeneous catalysis field.
Direct Synthesis of Palladium Catalyst on Supporting WS2 Nanotubes and its Reactivity in Cross-Coupling Reactions
Viic, Bojana,Cohen, Hagai,Popovitz-Biro, Ronit,Tenne, Reshef,Sokolov, Viacheslav I.,Abramova, Natalya V.,Buyanovskaya, Anastasiya G.,Dzvonkovskii, Sergei L.,Lependina, Olga L.
, p. 2234 - 2239 (2015)
Palladium nanoparticles were deposited on multiwall WS2 nanotubes. The composite nanoparticles were characterized by a variety of techniques. The Pd nanoparticles were deposited uniformly on the surface of WS2 nanotubes. An epitaxial relationship between the (111) plane of Pd and the (013) plane of WS2 was mostly observed. The composite nanoparticles were found to perform efficiently as catalysts for cross-coupling (Heck and Suzuki) reactions. The role of the nanotubes′ support in the catalytic process is briefly discussed.
The palladium(ii) complex of N,N-diethyl-1-ferrocenyl-3-thiabutanamine: Synthesis, solution and solid state structure and catalytic activity in Suzuki-Miyaura reaction
Damljanovi, Ivan,Stevanovi, Dragana,Pejovi, Anka,Ili, Danijela,ivkovi, Marija,Jovanovi, Jovana,Vukievi, Mirjana,Bogdanovi, Goran A.,Radulovi, Niko S.,Vukievi, Rastko D.
, p. 43792 - 43799 (2014)
In this paper we wish to present the first results on the synthesis of N,N-diethyl-1-ferrocenyl-3-thiabutanamine, its coordination with palladium(ii), the complete characterization of the thus obtained complex (including single crystal X-ray analysis for the complex in two polymorphic forms) and screening of its catalytic activity in Suzuki-Miyaura coupling of phenylboronic acid with several aryl bromides. The complex, either purified and then added to the reaction mixture or generated in situ, proved to be an excellent precatalyst in Suzuki-Miyaura coupling. The chemical behavior of the complex in solution was assessed by detailed NMR analyses and cyclic voltammetry measurements which allowed us to draw a number of mechanistic conclusions. This journal is
