Catalyst For Sonogashira Coupling Reactions Research Articles

Copper adorned magnetic nanoparticles as a heterogeneous catalyst for Sonogashira coupling reaction in aqueous media

A nanomagnetic hydrophilic heterogeneous copper catalyst, termed γ-Fe2O3@PEG@PAMAM G0-Cu, has been successfully prepared and characterized using FT–IR, XRD, FE-SEM, TEM, EDX, mapping, TGA/DTG, VSM and ICP analyses. The catalyst displayed excellent activity for the palladium-free Sonogashira cross coupling reaction of various aryl iodides and bromides with phenylacetylene derivatives in pure water. The presence of polyethylene glycol coupled with hydrophilic character of the Cu-catalyst adorned on γ-Fe2O3 MNPs provides the ready dispersion of the catalyst particles in water, leading to higher catalytic performance as well as facile catalyst recovery via simple magnetic decantation. The recovered catalyst was reused for at least six successive runs with little reduction in its catalytic activity and any noticeable changes in its structure. The use of water as a green solvent, without requiring any additive or organic solvent, as well as the exploitation of abundant and low-cost copper catalyst instead of expensive Pd catalyst along with the catalyst recovery and scalability, make this method favorable from environmental and economic points of view for the Sonogashira coupling reaction.

Highly Efficient and Reusable Polymer Supported Palladium Catalyst for Copper Free Sonogashira Reaction in Water

AbstractDevelopment of a novel, greener and efficient heterogeneous catalytic system for copper free Sonogashira reaction in water is described. This novel catalyst can be easily prepared by a simple method through synthetic modification of nitrile group in Polyacrylonitrile (PAN) using monoethanolamine (MEA) followed by its complexation with palladium chloride (PdCl2). The resulting polymer Pd complex (mPAN‐Pd) was characterized by means of Fourier Transform Infrared Spectroscopy (FTIR), Energy‐Dispersive X‐ray Spectroscopy (EDAX), Inductively Coupled Mass Spectrometry (ICP‐MS) and X‐ray Photo Electron Spectroscopy (XPS) analyses. mPAN‐Pd was then explored as highly efficient heterogeneous catalyst for Sonogashira coupling reaction under copper and ligand free conditions in water affording the corresponding coupling products up to 97 % isolated yield. Moreover, the catalyst was recovered by simple filtration after the reaction and reused for next 5 cycles with excellent stability and activity. This is the first report on the use of ethanolamine modified PAN Pd (II) complex as an efficient heterogeneous catalyst for a coupling reaction.

Pd nanoparticles loaded on modified chitosan-Unye bentonite microcapsules: A reusable nanocatalyst for Sonogashira coupling reaction

This work investigates the preparation of a catalytic complex of palladium nanoparticles supported on novel Schiff base modified chitosan-Unye bentonite microcapsules (Pd NPs@CS-UN). The complex has been characterized by FT-IR, EDS, XRD, TEM, HRTEM, Raman, ICP-OES and elemental mapping analyses. Pd NPs@CS-UN was used as a catalyst for Sonogashira coupling reactions between aryl halides and acetylenes, employing K2CO3 as the base and EtOH as a green solvent under aerobic conditions in which it showed high efficacy. Pd NPs@CS-UN was regenerated by filtration after the completion of the reaction. This catalytic process has many advantages including simple methodology, high yields, and easy work-up. The catalytic performance does not notably change even after five consecutive runs.

Decorated palladium nanoparticles on mesoporous organosilicate as an efficient catalyst for Sonogashira coupling reaction

Reforming mesoporous silica was provided by the reaction of SBA‐15 with (3-aminopropyl)triethoxysilane, the product of which was treated with furfural to give SBA-propyl-imine-furan. In the next step, palladium chloride was attached to the functionalized SBA‐15, so Pd nanoparticles immobilized on the mentioned catalyst for providing an applicable catalyst to use in the Sonogashira cross-coupling reaction. The high stability and performance of functionalized heterogeneous hybrid catalyst of Pd@SBA-Pr-imine-furan in overall were highly essential. The nano-structured Pd@SBA-Pr-imine-furan catalyst was studied for Sonogashira cross-coupling reaction by phenylacetylene and various aryl halides under reflux conditions with a small amount of catalyst. In comparison with the earlier reports, this paper offered several benefits such as short reaction times, high yields of products, catalyst stability, quick recovery, and catalytic activity for at least seven continuous runs.

Functionalized graphene oxide anchored to Ni complex as an effective recyclable heterogeneous catalyst for Sonogashira coupling reactions

The Sonogashira cross coupling reaction is an applied method for preparation of diarylethyne compounds from readily available aryl halide derivatives and phenyl acetylene. The coupling reaction using nickel complex of N,N′-Bis(2-hydroxyethyl)ethylenediamine onto core shell graphene oxide (GO@SiO2-BHED-Ni) as a catalyst was studied in this research. This heterogonous catalyst showed good thermal stability, highly efficiency and recyclability in the reaction. Moreover, the catalyst is simply separated and can be reused several times without significant loss of catalytic activity. A wide range of aryl halides was coupled successfully under palladium and phosphine free conditions. The use of this catalyst led to the formation of substituted aromatic alkynes in excellent yields and short reaction times.

Magnetically retrievable N-heterocyclic carbene-silver complex with wingtip ferrocenyl group for Sonogashira coupling

A new magnetically retrievable N-heterocyclic carbene-silver complex with wingtip ferrocenyl group has been prepared by multi-step procedure. The formation of complex was confirmed on the basis of analytical techniques such as FT-IR, Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), X-Ray diffraction (XRD), transmission electron microscopy (TEM) and VSM (vibrating sample magnetometer) analysis. The complex was successfully employed as an efficient heterogeneous catalyst for Sonogashira coupling reaction of aryl halides with terminal alkynes. The complex could be separated easily by applying external magnet. The reusability studies revealed that complex can be reused up to eight times without significant decrease in catalytic activity.

Reduced graphene oxide supported Cu2O nanoparticles as an efficient catalyst for Sonogashira coupling reaction

Reduced graphene oxide supported Cu2O nanoparticles were prepared by a liquid-phase reduction method and employed as an efficient heterogeneous catalyst for Sonogashira cross-coupling reaction. The catalyst exhibits high activity and selectivity towards the reaction of aryl halides with phenylacetylene under palladium-free and ligand-free conditions. Cu2O nanoparticles could activate phenylacetylene to produce copper(I) acetylide compounds, which subsequently react with aryl halides to form the corresponding disubstituted alkynes. The catalyst also shows a high stability and there is only slight decrease of activity after five cycles.

Characterization of a Poly-4-Vinylpyridine-Supported CuPd Bimetallic Catalyst for Sonogashira Coupling Reactions.

CuPd bimetallic solvated metal atoms (SMA) synthesized by metal vapor synthesis (MVS) technique and supported on poly-4-vinylpyridine (PVPy) resin, showed significantly higher catalytic activity in Sonogashira-type carbon-carbon coupling reactions than the corresponding monometallic Cu and Pd systems as well as their physical mixture. The analysis of the bimetallic catalyst combining transmission electron microscopy techniques and X-ray absorption fine structure (XAFS) spectroscopy revealed the presence of small Pd nanoparticles (dm =2.5 nm) while the analysis of the X-ray absorption data, at the Cu K-edge suggests the formation of thin and incomplete Cu oxide layers around the Pd-rich cores.

ChemInform Abstract: A Novel 1,2,4‐Triazine‐Functionalized Polystyrene Resin‐Supported Pd(II) Complex: A Copper‐ and Solvent‐Free Highly Efficient Catalyst for Sonogashira Coupling Reactions.

AbstractThe synthesis and characterisation of the heterogeneous catalyst is described.

A novel 1,2,4-triazine-functionalized polystyrene resin-supported Pd(II) complex: A copper- and solvent-free highly efficient catalyst for Sonogashira coupling reactions

A polystyrene-supported triazine palladium complex was prepared and characterized. The catalyst exhibits excellent catalytic activity and stability for the Sonogashira coupling reaction under ambient conditions. Various aryl halides were coupled with a number of terminal alkynes under air in the presence of 0.1 mol% of the catalyst to afford the corresponding coupled products in high yields. Furthermore, the heterogeneous catalyst can be readily recovered by simple filtration and reused for several times without a significant loss in its activity.

Copper- and phosphine-free Sonogashira coupling reactions of aryl iodides catalyzed by an N, N-bis(naphthylideneimino)diethylenetriamine-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions

A polymer-supported palladium(II) N, N-bis(naphthylideneimino)diethylenetriamine complex is found to be a highly active catalyst for Sonogashira coupling reactions. The reactions are performed under copper- and phosphine-free conditions in an air atmosphere. The palladium catalyst is easily separated, and can be reused several times without significant loss in catalytic activity.

Novel Pd-carrying composite carbon nanofibers based on polyacrylonitrile as a catalyst for Sonogashira coupling reaction

Abstract Novel Pd-carrying composite carbon nanofibers based on polyacrylonitrile were prepared by electrospinning and carbonization process. The catalytic activities of the composite nanofibers were tested with a Sonogashria coupling reaction of iodobenzene and phenylacetylene in liquid-phase. Transmission electron microscope and X-ray diffraction analyzer were used to characterize the nanofibers and the metal nanoparticles on the fibers; gas chromatograph and nuclear magnetic resonance spectroscopy were used to characterize the product of the testing reaction. The results first showed that the catalyst not only had a high catalytic activity, but also had good leaching-resistance, retrieval and reusability for the Sonogashira reaction.

A novel MCM-41-supported sulfur palladium(0) complex catalyst for Sonogashira coupling reaction

A novel MCM-41-supported sulfur palladium(0) complex was conveniently prepared from commercially available and cheap γ-mercaptopropyltriethoxysilane via immobilization on MCM-41, followed by reacting with palladium chloride and then the reduction with hydrazine hydrate. This complex exhibited excellent performance in Sonogashira coupling reaction.

Palladium nanowires stabilized by thiol-functionalized ionic liquid: seed-mediated synthesisand heterogeneous catalyst for Sonogashira coupling reaction

With the recent surge of the use of room-temperature ionic liquids in the synthesesof inorganic nanomaterials, we have successfully integrated the advantages of athiol-functionalized ionic liquid and the seed growth method to generate palladiumnanowires at room temperature. Moreover, the as-prepared palladium nanowires showvery high catalytic activity and stability for the Sonogashira coupling reaction.