52392-64-0Relevant articles and documents
Preparation and catalytic evaluation of a palladium catalyst deposited over two-dimensional zeolite ITQ-2 modified with N-donor groups
?těpni?ka, Petr,K?e?ková, Pavlína,Semler, Miloslav,?ejka, Ji?í
, p. 571 - 576 (2014)
Two-dimensional zeolite ITQ-2 was reacted successively with (3-chloropropyl)triethoxysilane, 2-(N,N-diethylamino)ethylamine, and ammonia to give a support bearing the =Si(CH2)3NHCH 2CH2NEt2 groups at the surface. Subsequent treatment with palladium(II) acetate afforded an immobilized palladium catalyst 3, which was tested in the Heck coupling of n-butyl acrylate with bromobenzene to give n-butyl cinnamate (4). This (pre)catalyst, which acts as a source of active metal species for the reaction occurring in the liquid phase, showed good activity in N,N-dimethylformamide and N,N-dimethylacetamide at 150 °C. Reaction tests with different bases revealed a pronounced effect of the base additive on the course of the catalyzed process in terms of both the activity (yield of the coupling product) and selectivity [amount of n-butyl 3,3-diphenylacrylate (5) resulting from twofold arylation]. Among the hydrated bases, the best yields of 4 were obtained in reactions performed in the presence of CH3CO2Na·3H2O and Na 3PO4·12H2O, while that with Na 2CO3·10H2O furnished considerably worse results. The use of the respective anhydrous bases not only decreased the yield of 4 but also incited the formation of the unwanted doubly arylated product 5.
Synthesis and activity evaluation of a FeCl2-promoted palladium hollow nano-sphere heterogeneous catalyst in Mizoroki–Heck coupling reactions
Abadi, Parvaneh Ghaderi-Shekhi,Hajian, Gelareh,Joshaghani, Mohammad,Nadri, Shirin,Rafiee, Ezzat
, p. 139 - 147 (2014)
A high-active, high-quality, and high-yield hollow Pd–PVP–Fe (palladium–poly(N-vinylpyrrolidone)–iron) nano-sphere catalyst with cubic structure was synthesized via a cheap method without using any support. This catalyst exhibited excellent catalytic activity in the Mizoroki–Heck reactions of less reactive chlorobenzene and some aryl bromides with n-butyl acrylate. The catalyst was fully characterized using SEM (scanning electron microscopy), EDX (energy dispersive X-ray spectroscopy), TEM (transmission electron microscopy), HRTEM (high resolution TEM), SAED (selected area electron diffraction) pattern, XRD (X-ray diffraction spectroscopy), FT-IR (Fourier transform infrared spectrophotometry), UV–Vis Spectrophotometry, Zeta sizer, and AAS (atomic absorption spectrometry). Effects of FeCl2·4H2O and PVP concentrations as well as their compatibility with palladium in the catalytic system were investigated. The catalytic property of the catalyst can be controlled by adjusting the proportion of Fe0, Pd0, and PVP concentration. The reused catalyst showed excellent activity as well as negligible leaching of the metal nanostructures into solution from the catalyst system.
Continuous microflow synthesis of butyl cinnamate by a Mizoroki-Heck reaction using a low-viscosity ionic liquid as the recycling reaction medium
Liu, Shifang,Fukuyama, Takahide,Sato, Masaaki,Ryu, Ilhyong
, p. 477 - 481 (2004)
A continuous microflow system was developed with efficient catalyst recycling for a Mizoroki-Heck reaction of iodobenzene with butyl acrylate, using a low-viscosity ionic liquid ([bmim]-NTf2) as the reaction medium. Using a CPC CYTOS Lab System
-
Kailan,Hardt
, p. 307,326 (1931)
-
Structure and Reactivity of "Unusual" N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts
Lebel, Helene,Janes, Marc K.,Charette, Andre B.,Nolan, Steven P.
, p. 5046 - 5047 (2004)
The reaction between palladium acetate and IMES·HCl leads to the formation of a novel palladium complex. The X-ray crystal structure analysis reveals that the palladium is C(2) bound to one NHC ligand (the normal binding mode), whereas the second ligand i
Palladium supported aminobenzamide modified silica coated superparamagnetic iron oxide as an applicable nanocatalyst for Heck cross-coupling reaction
Fatahi, Yousef,Ghaempanah, Aram,Ma?mani, Leila,Mahdavi, Mohammad,Bahadorikhalili, Saeed
, (2021/01/26)
An applicable palladium-based nanocatalyst was constructed through the immobilization of palladium onto 2-aminobenzamide functionalized silica coated superparamagnetic iron oxide magnetic nanoparticles. The nanocatalyst (named as Pd@ABA@SPIONs@SiO2) was characterized by several characterization methods, including scanning electron microscope (SEM), transmission electron microscopy (TEM), vibrating-sample magnetometry (VSM), energy-dispersive X-ray spectroscopy (EDS), dynamic light scattering (DLS), X-ray powder diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), inductively coupled plasma (ICP), and X-ray photoelectron spectroscopy (XPS) analyses. Microscopy results showed that the nanoparticles are spherical in shape with 20–25 nm size. The size of the nanoparticles was confirmed by the DLS method. The superparamagnetic nature of the catalyst was confirmed by the VSM method. The successful functionalization of SPIONs@SiO2 was confirmed by FT-IR spectroscopy. The presence of palladium in the structure of the nanocatalyst was illustrated by XRD and EDS analysis. Also using XPS technique, the oxidation state of palladium in Pd@ABA@SPIONs@SiO2 was determined zero before and after the catalyst was applied in Mizoroki-Heck reaction. Several aryl halides and alkenes were reacted in the presence of the nanocatalyst and formed the corresponding products in high isolated yields. The nanocatalyst showed very good reusability and did not decrease its activity after 10 sequential runs. Density functional theory (DFT) calculation was performed to provide a mechanism for the reaction and confirmed the role of the palladium catalyst in the reaction function.
NiFe2O4@SiO2@ZrO2/SO42-/Cu/Co nanoparticles: A novel, efficient, magnetically recyclable and bimetallic catalyst for Pd-free Suzuki, Heck and C-N cross-coupling reactions in aqueous media
Alavi G., Seyyedeh Ameneh,Nasseri, Mohammad Ali,Kazemnejadi, Milad,Allahresani, Ali,Hussainzadeh, Mahdi
, p. 7741 - 7757 (2021/05/13)
The novel heterogeneous bimetallic nanoparticles of Cu-Co were synthesized based on magnetic nanoparticles, and the magnetic nanocatalyst was characterized by XRD, FE-SEM, EDX mapping, BET, TEM, HRTEM, FTIR, TGA, and VSM. This catalyst was successfully applied as a recyclable magnetically catalyst in Heck, Suzuki, and C-N cross-coupling reactions with various aryl halides (iodides, bromides, and chlorides as challengeable substrates), with olefins, phenylboronic acid, and amines, respectively. We considered the rise of synergetic effects from the different Lewis acid and Br?nsted acid sites present in the catalyst. The catalyst was synthesized with cheap, available materials and a simple synthesis method. The catalyst can be separated easily using an external magnet. It was recycled for more than ten runs without a sensible loss of its catalytic activity, and no significant leaching of the Cu and Co quantity was observed. The significant benefits of the method are high-level generality, simple operation, and there are no heavy metals and toxic solvents. This is a quick, easy, efficacious and environmentally friendly protocol, and no by-products are formed in the reaction. These features make it an appropriate practical alternative protocol. In comparison with recent works, the other advantage of this catalyst is the synthesis of a wide variety of C-C and C-N bond derivatives (more than 40 derivatives). The other significant advantage is the low temperature of the reaction and the use of the least possible amount of the catalyst (0.003 g). The efficiency was good to excellent and the catalyst selectivity has been high. We aspire that our study inspires more interest to design novel catalysts based on using low-cost metal ions (such as cobalt and copper) in the cross-coupling reactions. This journal is
Palladium and silk fibroin-containing magnetic nano-biocomposite: a highly efficient heterogeneous nanocatalyst in Heck coupling reactions
Nouri Parouch, Ahmad,Koukabi, Nadiya,Abdous, Elham,Shobeiri, Seyed Amin
, p. 3165 - 3177 (2021/05/21)
Supported metal catalysts, for instance, palladium, are one of the foundations of chemical reactions, especially in C–C bond formation. The present study reports preparation of a magnetically separable palladium-supported nano-biocomposite with a low cost and easy immobilization technique. Fibroin, a natural biodegradable polymer, was used through an in situ method to cover the Fe3O4 nanoparticles to make a nano-biocomposite followed by anchoring palladium on the fibroin surface. The morphology and the structure of palladium-supported nano-biocomposite Fe3O4@fibroin-Pd were characterized by FT-IR, XRD, TGA, SEM, EDX, and TEM techniques. Consequently, the nanocatalyst activity was evaluated in the Heck coupling reactions. Only a very small amount of the nanocatalyst was employed in the reaction, and it showed excellent catalytic activity; in most cases more than 90% efficiency. The significant advantages of employing this nanocatalyst include high catalytic activity, short reaction times, easy separation of the nanocatalyst with an external magnet and great reusability. The results demonstrated that the used nanocatalysts were very active for four consecutive reaction rounds.
