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
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Kailan,Hardt
, p. 307,326 (1931)
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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
Pd supported on clicked cellulose-modified magnetite-graphene oxide nanocomposite for C-C coupling reactions in deep eutectic solvent
Karimi, Sabah,Masteri-Farahani, Majid,Niakan, Mahsa,Shekaari, Hemayat
, (2020/10/02)
Cellulose-modified magnetite-graphene oxide nanocomposite was prepared via click reaction and utilized for immobilization of palladium (Pd) nanoparticles without using additional reducing agent. The abundant OH groups of cellulose provided the uniform dispersion and high stability of Pd nanoparticles, while magnetite-graphene oxide as a supporting material offered high specific surface area and easy magnetic separation. The as-prepared nanocomposite served as a heterogeneous catalyst for the Heck and Sonogashira coupling reactions in various hydrophilic and hydrophobic deep eutectic solvents (DESs) as sustainable and environmentally benign reaction media. Among the fifteen DESs evaluated for coupling reactions, the hydrophilic DES composed of dimethyl ammonium chloride and glycerol exhibited the best results. Due to the low miscibility of catalyst and DES in organic solvents, the separated aqueous phase containing both of the catalyst and DES can be readily recovered by evaporating water and retrieved eight times with negligible loss of catalytic performance.
A comparative study of palladium-based coordination compounds with bidentate (N,N, P,P and P,O) ligands; Design, synthesis, X-ray structural, catalytic activity and DFT studies
Babaee, Heshmatollah,Javad Sabounchei, Seyyed,Naghipour, Ali,Notash, Behrouz,Sayadi, Mohsen,Sedghi, Asieh
, (2020/10/13)
This account describes our recent studies on four new asymmetric cyclometallated Pd(II) complexes with a formula [L1 → Pd ← L2](ClO4) (L1 = benzylamine and L2 = bis (diphenylphosphino) methane oxide (
Introduction of a Recyclable Basic Ionic Solvent with Bis-(NHC) Ligand Property and The Possibility of Immobilization on Magnetite for Ligand- and Base-Free Pd-Catalyzed Heck, Suzuki and Sonogashira Cross-Coupling Reactions in Water
Min, Qingwang,Miao, Penghua,Chu, Deyu,Liu, Jinghan,Qi, Meijuan,Kazemnejadi, Milad
, p. 3030 - 3047 (2021/02/16)
A new versatile and recyclable NHC ligand precursor has been developed with ligand, base, and solvent functionalities for the efficient Pd-catalyzed Heck, Suzuki and Sonogashira cross-coupling reactions under mild conditions. Furthermore, NHC ligand precursor was immobilized on magnetite and its catalytic activity was also evaluated towards the coupling reactions as a heterogeneous catalyst. The NHC ligand precursor was prepared with imidazolium functionalization of TCT followed by a simple ion exchange by hydroxide ions. However, the results revealed an excellent catalytic activity for the both homogeneous and heterogeneous catalytic systems. 1.52?g.cm?3 and 1194 cP was obtained for the density and viscosity of the NHC ligand precursor respectively. On the other hand, the heterogeneous type could be readily recovered from the reaction mixture and reused for several times while preserving its properties. Heterogeneous nature of the magnetic catalyst was studied by hot filtration, mercury poisoning, and three-phase tests. High to excellent yields were obtained for all entries for the both homogeneous and heterogeneous catalysts, which reflects the high consistency of the catalyst. Graphic Abstract: [Figure not available: see fulltext.]
