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.
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.
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.].
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.
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.
Fe(OTf)3-mediated synthesis of sulfonyl dihydropyrans
Chang, Meng-Yang,Chen, Yu-Hsin,Cheng, Yu-Chieh
, p. 518 - 524 (2016)
Fe(OTf)3-mediated one-pot (3+3) cycloaddition of β-ketosulfones 1 with prenyl alcohol (2) in MeNO2 affords sulfonyl dihydropyrans 5 in good yields via a sequential intermolecular α-prenylation followed by intramolecular Friedel-Crafts alkylation. The method provides a highly effective condition.
In situ generation of supported palladium nanoparticles from a Pd/Sn/S chalcogel and applications in 4-nitrophenol reduction and Suzuki coupling
Shan, Xinyao,Sui, Ning,Liu, Wengang,Liu, Manhong,Liu, Jian
, p. 4446 - 4450 (2019)
Supported ultrafine palladium nanoparticles with uniform distribution exhibit remarkable catalytic capabilities in various applications. Obtaining size-controlled Pd nanoparticles on a support remains challenging and here we present a one-step in situ route to well-defined Pd nanoparticles through reduction of a Pd-containing chalcogel (Pd/Sn/S) with tunable size distribution. The spacings of the Pd nanoparticles on the chalcogel can be controlled by using antimony-containing chalcogels (Pd-Sb/Sn/S). The catalytic performance of Pd nanoparticles supported on the chalcogel surface was assessed in 4-nitrophenol reduction and the Suzuki-Miyaura coupling reaction, and found to exhibit good activities and robust stability. This in situ and one-step synthetic method could be further extended to synthesize a series of noble metal nanoparticles for a variety of applications.
In-situ synthesis of a palladium-polyaniline hybrid catalyst for a Suzuki coupling reaction
Islam, Rafique Ul,Witcomb, Michael J.,Van Der Lingen, Elma,Scurrell, Michael S.,Van Otterlo, Willem,Mallick, Kaushik
, p. 2206 - 2210 (2011)
Palladium-catalyzed cross-coupling reactions are one of the most frequently used synthetic tools for the construction of new carbon-carbon bonds in organic synthesis. The present study describes the use of palladium-polyaniline composite material as a catalyst for the Suzuki coupling of aryl halides. Palladium-polyaniline nanocomposite material was synthesized using an in-situ technique in which palladium acetate and aniline hydrochloride were used as the precursors of the composite. Electron microscopy imaging showed that the palladium particles were well-dispersed within the polymer matrix and were typically 3-5 nm in diameter. The metal-polymer composite material was used as a catalyst for the coupling of phenylboronic acid with aryl halides in the presence of an inorganic base and showed excellent yield with high TOF values.
Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives
Das, Tapas Kumar,Kundu, Mrinalkanti,Mondal, Biswajit,Ghosh, Prasanjit,Das, Sajal
, p. 208 - 218 (2021/12/29)
A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.
Lipids as versatile solvents for chemical synthesis
Bayer, Annette,Gevorgyan, Ashot,Hopmann, Kathrin H.
supporting information, p. 7219 - 7227 (2021/09/28)
Development of safe, renewable, cheap and versatile solvents is a longstanding challenge in chemistry. We show here that vegetable oils and related systems can become prominent solvents for organic synthesis. Suzuki-Miyaura, Hiyama, Stille, Sonogashira and Heck cross-couplings proceed with quantitative yields in a range of vegetable oils, fish oil, butter and waxes used as solvents. Appropriate methodologies for high-throughput screening and sustainable isolation techniques applicable for vegetable oils and related lipids are presented.
Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki-Miyaura cross-coupling reactions
Holzapfel, Cedric W.,Lamola, Jairus L.,Maumela, Munaka Christopher,Moshapo, Paseka T.
, p. 26883 - 26891 (2021/08/17)
A family of biaryl phosphacyclic ligands derived from phobane and phosphatrioxa-adamantane frameworks is described. The rigid biaryl phosphacycles are efficient for Suzuki-Miyaura cross-coupling of aryl bromides and chlorides. In particular, coupling reactions of the challenging sterically hindered and heterocyclic substrates were viable at room temperature.
