Recyclable Catalyst For Heck Reaction Research Articles

One‐pot synthesis of magnetic palladium–NiFe2O4–graphene oxide composite: an efficient and recyclable catalyst for Heck reaction

A magnetically separable NiFe2O4@GO–Pd composite (GO = graphene oxide) was successfully prepared by a facile one‐pot hydrothermal strategy. This new kind of hybrid material was fully characterized using powder X‐ray diffraction, Raman spectroscopy, X‐ray photoelectron spectroscopy, transmission electron microscopy and vibrating sample magnetometry. Structural characterizations confirmed the formation of NiFe2O4 and Pd nanocrystals, and the close anchoring between nanoparticles and GO sheets. Additionally, the as‐prepared NiFe2O4@GO–Pd nanocomposite was effectively employed in the palladium‐catalyzed Heck reaction in an ethanol–water system as a green solvent. The catalyst was completely recoverable with the simple application of an external magnetic field and with no obvious loss of catalytic activity even after six repeated cycles. Copyright © 2016 John Wiley & Sons, Ltd.

Green synthesis of palladium nanoparticles via branched polymers: a bio-based nanocomposite for C–C coupling reactions

Renewable and sustainable CMH was the natural ligand for CMH–Pd(0) nanocomposite which was as an efficient and recyclable catalyst for Heck reaction.

Cobalt nanoparticles supported on ionic liquid‐functionalized multiwall carbon nanotubes as an efficient and recyclable catalyst for Heck reaction

A novel and environmentally friendly cobalt nanoparticle catalyst supported on ionic liquid‐functionalized multiwall carbon nanotubes was successfully prepared and evaluated as a heterogeneous catalyst for the Mizoroki–Heck reaction. Several reaction parameters, including type and amount of solvent and base, were evaluated. This nanocatalyst could also be recovered and reused at least six times without any discernible decrease in its catalytic activity. Copyright © 2015 John Wiley & Sons, Ltd.

Fiber-Palladium Complex as Highly Active and Recyclable Catalyst for Heck Reaction in Air

Fiber-Palladium Complex as Highly Active and Recyclable Catalyst for Heck Reaction in Air

Hyperbranched Polyethylenes Encapsulating Self-Supported Palladium(II) Species as Efficient and Recyclable Catalysts for Heck Reaction

We demonstrate in this paper a unique self-supporting strategy for the synthesis of hyperbranched polyethylenes (HBPEs) encapsulating Pd(II) species as efficient and recyclable catalysts for Heck reaction. This strategy combines remarkably the synthesis of HBPE polymer support and the immobilization of Pd(II) species in situ in one pot. It is achieved by chain walking copolymerization of ethylene with an acrylate comonomer (2) containing a disulfide functionality with a cationic Pd(II)–diimine catalyst (1). The copolymerization renders successfully HBPEs containing pendant disulfide groups at a controllable content, while with no poisoning effect from the disulfide functionality. Meanwhile, the Pd(II) catalyst in situ immobilizes itself onto the polymers by coordinative binding with the pendant disulfide groups, giving rise to the homogeneous self-supported Pd(II) catalysts. The resulting Pd-containing HBPEs having a low content of 2 (ca. < 1 mol %) have been found to be efficient and recyclable catalysts...

Pd Nanoparticles in the Thermoregulated Ionic Liquid and Organic Biphasic System: An Efficient and Recyclable Catalyst for Heck Reaction

A thermoregulated ionic liquid and organic biphasic system composed of ionic liquid [CH3(OCH2CH2)16N+Et3][CH3SO3 −] (ILPEG750) with ILPEG750-stabilized Pd nanoparticles and organic solvents, which allows for not only a highly efficient homogeneous catalytic reaction, but also an easy biphasic separation and reuse of catalyst attributed to the thermoregulated phase-transition property of the system, was employed for Heck reaction. The ILPEG750-stabilized Pd nanoparticle catalyst exhibited high efficiency, more importantly, after reaction the Pd nanoparticle catalyst could be separated from products by simple phase separation and recycled for six times without evident loss of activity. A thermoregulated ionic liquid and organic biphasic system containing [CH3(OCH2CH2)16N+Et3][CH3SO 3 - ] (ILPEG750)-stabilized Pd nanoparticles was applied to Heck reaction for the first time. The Pd nanoparticle catalyst exhibited high efficiency and good recyclability.

Ethylenediamine-functionalized activated carbon anchored palladium complex: a recyclable catalyst for Heck reaction

Ethylenediamine-functionalized activated carbon anchored palladium catalyst was prepared via grafting ethylenediamine onto chemically modified activated carbon, followed by the reaction with palladium chloride and then the reduction with potassium borohydride. Fourier transform infrared spectroscopy and X-ray photoelectron spectroscopy results indicated that palladium immobilized on the carrier via coordination bond in this catalyst. Transmission electron microscopy images showed that the supported palladium is in the form of near spherical particles smaller than 10 nm diameter and evenly dispersed on the surface of the carrier. This catalyst was applied for the Heck reaction of aryl halides with olefins. The influences of solvents, bases, reaction temperatures and times on catalytic property of the catalyst were investigated by using the coupling of iodobenzene and styrene as a probe reaction. By varying the combination of aryl halides and olefins, this catalyst showed effective catalytic activities to produce corresponding coupling products with moderate to excellent yields. Moreover, it can be recovered by simple filtration and reused several times without significant loss of activity and selectivity.

The Ionic Palladium Porphyrin as a Highly Efficient and Recyclable Catalyst for Heck Reaction in Ionic Liquid Solution Under Aerobic Conditions

The ionic palladium porphyrin featured with pyridinium tags at four meso-positions, palladium tetrakis-(N-methyl-4-pyridinium)-porphyrin iodide ([Pd(II)TMPy)P][I]4 (3), embedded in the similar structured ionic liquid of N-butyl pyridinium tetrafluoroborate ([Bpy]BF4) was found to be a highly efficient and recyclable catalytic system for the Heck cross-coupling of iodobenzene (derivatives) and ethyl acylate, with high turnover frequency of 56,000 h−1 under aerobic conditions. The active charge transfer transition occurred in 3-[Bpy]BF4 system during the Heck reaction could account for the efficiency in the catalytic coupling, which was observed in the UV–visible spectra.

Konjac glucomannan supported palladium complex: An efficient and recyclable catalyst for Heck reaction

Konjac glucomannan supported palladium catalyst was prepared and applied for Heck arylation reaction of conjugate alkenes with aryl halides, to afford corresponding cross-coupling products in good to excellent yields. The catalyst was recovered by simple filtration and reused for five times without loss of activity.

Polyvinyl chloride–polyethylene–polyamine supported palladium complexes as high efficient and recyclable catalysts for Heck reaction

Two kinds of polyvinyl chloride–polyethylene–polyamine supported palladium complexes were synthesized and characterized by XPS, TG, DTA, TEM, etc. These complexes are efficient catalysts for Heck reaction of acrylic acid with aryl iodides in air at the low temperature (50 °C) using 0.125 mol% of the catalysts. Effect of amount of the catalyst indicates that the Heck reaction acrylic acid with iodobenzene can be carried out with tiny amount of the catalyst (0.02%) at 90 °C. The complexes have high thermal stability and can be easily recovered and reused. Yields of making cinnamic acid were even high as 68.3 and 78.0% respectively for Heck reaction of acrylic acid with iodobenzene by using the two complexes that were recovered for 12 times.

Palladium Bipyridyl Complex Anchored on Nanosized MCM‐41 as a Highly Efficient and Recyclable Catalyst for Heck Reaction.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Palladium nanoparticles in poly(ethyleneglycol): the efficient and recyclable catalyst for Heck reaction

Palladium nanoparticles with narrow size distribution were prepared by applying poly(ethyleneglycol) (PEG) and Pd(OAc) 2 in the absence of other chemical agents. PEG appeared to act as both reducing agent and stabilizer. The results of XRD show that the concentration of precursor played the key role to the development of palladium nanoparticles. The reduction of Pd 2+ to nano Pd was sensitive to the chain length of the PEG, and the larger chain length PEG such as PEG 2000 exhibited higher reduction reactivity. The as-prepared palladium nanoparticles were found to be a highly stable and reusable catalyst for Heck reaction.

Palladium bipyridyl complex anchored on nanosized MCM-41 as a highly efficient and recyclable catalyst for Heck reaction

Palladium bipyridyl complex anchored inside the channels of nanosized MCM-41 silicas was found to be a highly efficient and recyclable catalyst for the Heck reaction with a turnover number up to 106 for each cycle.

New Aliphatic C-Metallated Palladacycle in the Pores of 3-Hydroxypropyl Triethoxysilane Functionalized MCM-41

A new aliphatic C-metallated palladacycle has been prepared in the pores of 3-hydroxypropyl triethoxysilane functionalized MCM-41 and has been found to be a superior recyclable catalyst for Heck reaction. The thermal stability of the palladated material was found to be higher than that of the nonpalladated starting material.