- Multi-functionalized ionic liquid with in situ-generated palladium nanoparticles for Suzuki, Heck coupling reaction: a comparison with deep eutectic solvents
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Abstract: A new catalytic system for Suzuki and Heck coupling has been developed from multi-functionalized task specific ionic liquid (TSIL) and in situ formed palladium nanoparticles (PdNps). The generated PdNPs were characterized by UV–Visible spectroscopy and transmission electron microscopy (TEM) analysis. These PdNPs have found size below 10?nm and exhibited a excellent catalytic activity in the cross-coupling of aryl halide without using external phosphine ligand. Along with electron deficient olefins, electron rich olefins were also undergo smooth reaction giving excellent yield. The results obtained in ionic liquid are compared with results obtained in deep eutectic solvents. Progress of reaction was found very smooth in ionic liquid rather than in deep eutectic solvents. The aqueous system containing ionic liquid along with PdNPs was recycled for seven times, without any significant loss. Graphical abstract: [Figure not available: see fulltext.].
- Gaikwad,Undale,Patil,Pore
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p. 253 - 261
(2019/01/30)
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- Synthesis of a novel ZnO nanoplates supported hydrazone-based palladacycle as an effective and recyclable heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction
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A new hydrazone-based palladacycle complex was successfully prepared onto ZnO nanoplates support and was fully identified by using a variety of methods such as energy dispersive X-ray spectroscopy (EDX), Brunauer-Emmett-Teller analysis (BET), inductively coupled plasma technique (ICP), thermogravimetric analysis (TGA), Fourier transform infrared spectroscopy (FT-IR) and X-ray photoelectron spectroscopy (XPS). The morphology of nanoplates support has been also confirmed by scanning electron microscopy (SEM) and powder X-ray diffraction (XRD). Furthermore, it was shown that ZnO nanoplates supported hydrazone-based palladacycle can act as a highly efficient heterogeneous catalyst for the Mizoroki-Heck cross-coupling reaction with excellent yields. The reaction was successfully carried out between aryl iodides, bromides or even aryl chlorides with a variety of olefins. Additionally, it is possible to isolate the catalyst from the reaction mixture and reused for eight sequential cycles without remarkable decrease in catalytic activity.
- Nouri, Fatemeh,Rostamizadeh, Shahnaz,Azad, Mohammad
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p. 664 - 673
(2017/12/15)
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- Phosphanamine-functionalized magnetic nanoparticles (PAFMNP): An efficient magnetic recyclable ligand for the Pd-catalyzed Heck reaction of chloroarenes
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A phosphanamine-functionalized trimethoxysilyl compound (DPPPA) was synthesized and reacted with magnetic nanoparticles in order to synthesise a novel magnetic reusable phosphanamine ligand (PAFMNP) for application in transition metal-catalyzed coupling reactions. The Pd complex of PAFMNP (Pd-PAFMNP) was found to be an efficient heterogeneous catalyst for the Heck reaction of aryl chlorides. Only 1.0 mol% of catalyst was needed to accomplish the Heck reaction of the aryl chlorides. The catalyst was reusable at least 5 times without a significant decrease in its catalytic activity.
- Panahi, Farhad,Zarnaghash, Narges,Khalafi-Nezhad, Ali
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p. 1250 - 1255
(2016/02/19)
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- Immobilized Pd(0) nanoparticles on phosphine-functionalized graphene as a highly active catalyst for Heck, Suzuki and N-arylation reactions
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In this study, a phosphine group was chemically grafted to the surface of graphene in order to prepare a reusable ligand with high surface area, incorporating a phosphine moiety. The treatment of graphene oxide (GO) with hydroxide followed by an aqueous work-up yields an OH-functionalized graphene material (GOH) via ring-opening of the epoxide groups. Reaction of GOH with chlorodiphenylphosphine (ClPPh2) gives a new material, GOPPh2 (PFG), which can be used for stabilization of metal nanoparticles or complexation of transition metals in order to prepare a reusable metal catalyst. Stabilization of palladium nanoparticles on the surface of GOPPh2 resulted in the production of an efficient heterogeneous Pd catalyst (PFG-Pd) for application in C-C and C-N bond formation reactions. The PFG-Pd catalyst was characterized using some different microscopic and spectroscopic techniques such as FT-IR, XRD, TEM, SEM, EDX, and ICP analysis. The applicability of the PFG-Pd catalyst was evaluated in Heck, Suzuki and N-arylation reactions. The catalyst system showed high catalyst activity in these processes and the target products were obtained in high isolated yields. The PFG-Pd catalyst was reusable in these reactions for at least 5 times with no significant decrease in its catalytic activity.
- Fareghi-Alamdari, Reza,Haqiqi, Mohsen G.,Zekri, Negar
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p. 1287 - 1296
(2016/02/19)
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- An efficient approach to alkenyl nitriles from allyl esters
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A novel and efficient approach to alkenyl nitriles from allyl esters has been developed. A tandem Pd-catalyzed substitution and the subsequent oxidative rearrangement are involved in this transformation. The method provides an important supplement for the synthesis of alkenyl nitriles from allyl esters. Georg Thieme Verlag Stuttgart · New York.
- Zhou, Wang,Xu, Jiaojiao,Zhang, Liangren,Jiao, Ning
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supporting information; experimental part
p. 887 - 890
(2011/06/17)
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- Binaphthyl-bridged bis-imidazolinium salts as N-heterocyclic carbene ligand precursors in the palladium-catalyzed Heck reaction
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Two new bis-imidazolinium salts (4a, 4b) have been synthesized as precursors of N-heterocyclic carbenes (NHCs) from the commercially available (R)-2,2′-dihydroxy-1,1′-binaphthalene. The two bis-imidazolinium salts were used as efficient precursor of NHC ancillary ligands in the palladium-catalyzed Heck reaction. Good to excellent yields and high stereoselectivities were obtained with ethyl acrylate, acrylonitrile, and acrylamide as starting materials. The structure of bis-imidazolinium salt 4b was further characterized by single crystal X-ray diffraction analysis. Science China Press and Springer-Verlag Berlin Heidelberg 2011.
- Wu, Hui,Jin, Can,Huang, Guoli,Wang, Lianjun,Jiang, Juli,Wang, Leyong
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experimental part
p. 951 - 956
(2012/02/05)
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- Mizoroki-Heck cross-couplings of 2-acetyl-5-bromobenzofuran and aryl halides under microwave irradiation
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Mizoroki-Heck cross-coupling reactions of 2-acetyl-5-bromobenzofuran as well as activated and deactivated aryl bromides with various olefins were investigated under both thermal as well as microwave irradiating conditions in open air using water solvent.
- Shaaban, Mohamed R.,Darweesh, Ahmed F.,Dawood, Kamal M.,Faraga, Ahmad M.
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experimental part
p. 208 - 225
(2011/02/22)
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- Carbon-carbon cross-coupling reactions under continuous flow conditions using poly(vinylpyridine) doped with palladium
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Coordinative immobilization of an oxime-based pallada-cycle to poly(vinylpyridine)/glass composite materials shaped as Raschig rings or placed within the PASSflow microreactor affords technical devices that are well suited for performing palladium-catalyzed carbon-carbon cross-coupling reactions in the flow-through mode. Reusability of the immobilized precatalyst as well as applications in the microwave field were investigated. Experiments with thiol- and pyridine-based scavengers were carried out, which revealed that the active palladium species is likely to be composed of nanoparticles of unknown nature and that the poly(vinylpyridine) carrier has scavenging properties for these particles. Georg Thieme Verlag Stuttgart.
- Mennecke, Klaas,Solodenko, Wladimir,Kirschning, Andreas
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experimental part
p. 1589 - 1599
(2009/04/03)
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- Design and development of a new chelating bis(phosphinite)-based palladium(II) catalyst and its application to the heck reaction
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A new sterically demanding and bulky bis(phosphinite) ligand derived from salicylaldehyde and 2-amino-3-hydroxy pyridine and its palladium(II) complex has been synthesized and characterized. The utility of this palladium complex has been demonstrated in the Heck reaction between a variety of aryl halides and olefin substrates. Georg Thieme Verlag Stuttgart.
- Pathak,Maheswaran,Leon Prasanth,Lakshmi Kantam
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p. 757 - 760
(2007/12/27)
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- First palladium-catalyzed Heck reactions with efficient colloidal catalyst systems
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For the first time it has been shown that palladium colloids are effective and active catalysts for the olefination of aryl bromides (Heck reaction). Worthy of note are the high activities of the catalyst system for activated aryl bromides under optimized reaction conditions, which are better than or comparable with classical palladium phosphine complexes. Addition of phosphines strongly retards the reaction rate of the colloid catalyst. Nevertheless, this type of catalyst is not suitable for the activation of non-activated substrates, especially technically interesting aryl chlorides.
- Beller, Matthias,Fischer, Hartmut,Kuehlein, Klaus,Reisinger,Herrmann
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p. 257 - 259
(2007/10/03)
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- Transmission of substituent effects through extended systems-I. p-Substituted cinnamonitriles
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Infrared data, 13C chemical shifts and ab-initio calculations are reported for a series of p-substituted cinnamonitriles.The i.r. values include intensities for the benzene, ethylene and cyanide vibrations which allow an estimation of resonance effects.The relative importance of the various mechanisms of transmission of electronic effects are discussed.
- Butt, G.,Topsom, R. D.
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p. 811 - 818
(2007/10/02)
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