40458-57-9Relevant academic research and scientific papers
Stabilization of palladium catalysts for the heck reaction by support functionalization and solvent selection
Oliveira, Rafael L.,Hooijmans, Jasper B.F.,De Jongh, Petra E.,Klein Gebbink, Robertus J.M.,De Jong, Krijn P.
, p. 3223 - 3230 (2014)
Pd nanoparticles were synthesized on nonfunctionalized and functionalized SBA-15 grafted with thiol or amine groups. The resulting materials were used as catalysts to study the influence of these functional groups for a similar Pd particle size of approxi
Schiff base complex of palladium immobilized on magnetic nanoparticles: an efficient and recyclable nanocatalyst for C?C coupling reactions
Rezaei, Somaieh,Ghorbani-Choghamarani, Arash,Badri, Rashid
, p. 985 - 990 (2016)
A Schiff base complex of palladium anchored on Fe3O4 magnetic nanoparticles as an efficient and magnetically reusable nanocatalyst is reported for C?C bond formation through Heck and Suzuki reactions. The catalyst was easily recovere
Nanomagnetic Salamo-based-Pd(0) Complex: an efficient heterogeneous catalyst for Suzuki–Miyaura and Heck cross-coupling reactions in aqueous medium
Ansari, Mohammad Javed,Jasim, Saade Abdalkareem,Majdi, Hasan Sh.,Opulencia, Maria Jade Catalan,Uktamov, Khusniddin Fakhriddinovich
, (2022/04/21)
In order to develop a magnetic nanocatalyst, an asymmetric salamo-based-Palladium(0) complex grafted on Fe3O4 MNPs was synthesized and characterized using physicochemical methods including FT-IR, XRD, SEM, TEM, EDS, ICP-AES, X-ray mapping, TGA and VSM analyses. Catalytic activities of [Fe3O4@H2L-Pd (0)] were examined towards two catalytic reactions: a) synthesis of biaryls via the Suzuki C-C cross-coupling of phenylboronic acid with aryl halides and b) one-pot synthesis of butyl cinnamates via the Heck C-C cross-coupling of butyl acrylate with aryl halides under green conditions in aqueous medium. Moreover, the effects of the catalyst amount, reaction temperature, type of the solvent and nature of base on catalytic activity were investigated. The [Fe3O4@H2L-Pd(0)] nanocatalyst was recycled for at least six consecutive reaction cycles without a significant loss of its catalytic activity. This illustrates the sustainable anchoring of palladium(0) on Fe3O4.
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.]
S,O-Functionalized Metal-Organic Frameworks as Heterogeneous Single-Site Catalysts for the Oxidative Alkenylation of Arenes via C-H activation
Bals, Sara,Bugaev, Aram L.,Dallenes, Jesse,De Vos, Dirk E.,Henrion, Micka?l,Krajnc, Andra?,Liu, Pei,Mali, Gregor,Soldatov, Alexander V.,Van Velthoven, Niels
, p. 5077 - 5085 (2020/05/27)
Heterogeneous single-site catalysts can combine the precise active site design of organometallic complexes with the efficient recovery of solid catalysts. Based on recent progress on homogeneous thioether ligands for Pd-catalyzed C-H activation reactions, we here develop a scalable metal-organic framework-based heterogeneous single-site catalyst containing S,O-moieties that increase the catalytic activity of Pd(II) for the oxidative alkenylation of arenes. The structure of the Pd?MOF-808-L1 catalyst was characterized in detail via solid-state nuclear magnetic resonance spectroscopy, N2 physisorption, and high-angle annular dark field scanning transmission electron microscopy, and the structure of the isolated palladium active sites could be identified by X-ray absorption spectroscopy. A turnover frequency (TOF) of 8.4 h-1 was reached after 1 h of reaction time, which was 3 times higher than the TOF of standard Pd(OAc)2, ranking Pd?MOF-808-L1 among the most active heterogeneous catalysts ever reported for the nondirected oxidative alkenylation of arenes. Finally, we showed that the single-site catalyst promotes the oxidative alkenylation of a broad range of electron-rich arenes, and the applicability of this heterogeneous system was demonstrated by the gram-scale synthesis of industrially relevant products.
A new approach to large scale production of dimethyl sulfone: A promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions
Cheng, Shen,Wei, Wei,Zhang, Xingyu,Yu, Hewei,Huang, Mingming,Kazemnejadi, Milad
, p. 2069 - 2076 (2020/04/07)
Dimethyl sulfone (DMSN) was easily prepared through efficient oxidation of dimethyl sulfoxide (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3/NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C-C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity.
Structure?Activity Relationships of Cinnamate Ester Analogues as Potent Antiprotozoal Agents
Bernal, Freddy A.,Kaiser, Marcel,Wünsch, Bernhard,Schmidt, Thomas J.
, p. 68 - 78 (2019/11/22)
Protozoal infections are still a global health problem, threatening the lives of millions of people around the world, mainly in impoverished tropical and sub-tropical regions. Thus, in view of the lack of efficient therapies and increasing resistances against existing drugs, this study describes the antiprotozoal potential of synthetic cinnamate ester analogues and their structure-activity relationships. In general, Leishmania donovani and Trypanosoma brucei were quite susceptible to the compounds in a structure-dependent manner. Detailed analysis revealed a key role of the substitution pattern on the aromatic ring and a marked effect of the side chain on the activity against these two parasites. The high antileishmanial potency and remarkable selectivity of the nitro-aromatic derivatives suggested them as promising candidates for further studies. On the other hand, the high in vitro potency of catechol-type compounds against T. brucei could not be extrapolated to an in vivo mouse model.
Boehmite@tryptophan-Pd nanoparticles: A new catalyst for C–C bond formation
Ghorbani-Choghamarani, Arash,Mohammadi, Masoud,Hudson, Robert H.E.,Tamoradi, Taiebeh
, (2019/06/24)
A boehmite@tryptophan-Pd nanoparticulate catalyst was prepared by a simple, fast and convenient route. The nanomaterial was characterized using various techniques and employed as a thermally stable catalyst for Heck, Stille and Suzuki cross-coupling reactions. Optimized conditions for these reactions are described. The catalyst could be isolated, post-reaction, by simple filtration and recycled for several consecutive cycles without a notable change in its activity.
Bis-salophen palladium complex immobilized on Fe3O4@SiO2 nanoparticles as a highly active and durable phosphine-free catalyst for Heck and copper-free Sonogashira coupling reactions
Sardarian, Ali Reza,Kazemnejadi, Milad,Esmaeilpour, Mohsen
, p. 3132 - 3145 (2019/03/06)
New Fe3O4@SiO2 core-shell superparamagnetic nanoparticles functionalized by a bis-salophen Schiff base Pd complex were synthesized and employed as an efficient magnetic nanocatalyst in the Heck and Sonogashira cross coupling reactions. The synthesized nanostructures were characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), dynamic light scattering (DLS), energy dispersive X-ray analysis (EDX), X-ray photoelectron spectroscopy (XPS), elemental analysis (CHN), cyclic voltammetry (CV), Brunauer-Emmett-Teller analysis (BET), and UV-vis spectroscopy. The morphology and size of the nanoparticles were investigated by FE-SEM and TEM analyses. Furthermore, the magnetic properties of the catalyst were investigated by VSM analysis. The loading content and leaching amounts of palladium on the catalyst were measured by inductively coupled plasma (ICP) analysis. Also, the thermal behavior of this magnetic heterogeneous catalyst was studied using a TGA instrument. This heterogeneous catalytic system showed a good performance in the coupling of aryl halides with alkynes (Sonogashira reaction) as well as aryl halides with alkene derivatives (Heck reaction). High to excellent yields were achieved for these C-C coupling reactions. The catalyst can be simply separated from the reaction media by an external magnet and reused for eight consecutive runs without any significant loss of activity. Finally, the kinetics of the reactions were studied in this work.
Green, cost-effective and efficient procedure for Heck and Sonogashira coupling reactions using palladium nanoparticles supported on functionalized Fe3O4@SiO2 by polyvinyl alcohol as a highly active, durable and reusable catalyst
Sardarian, Ali Reza,Eslahi, Hassan,Esmaeilpour, Mohsen
, (2019/05/28)
A novel heterogenized organometallic catalyst was synthesized by coordinating palladium with polyvinyl alcohol-functionalized Fe3O4@SiO2 nanospheres. This novel catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscope, field emission scanning electron microscope, dynamic light scattering, UV–vis spectroscopy, X-ray photoelectron spectroscopy, energy dispersive X-ray analysis, thermogravimetric analysis and inductively coupled plasma analysis. The prepared palladium nanoparticles supported on polyvinyl alcohol functionalized Fe3O4@SiO2 nanoparticles were successfully applied as a magnetically recyclable catalyst in Heck and Sonogashira coupling reactions in water. They showed remarkable activity toward aryl halides (I, Br, Cl) using very low palladium loading in excellent yields and demonstrated high TONs (mmol of product per mmol of catalyst). Also, the catalyst could be magnetically separated and reused seven times without any appreciable loss of catalytic activity.
