Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction
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Keywords:
Coupling reaction
Thermogravimetric analysis
Phenylboronic acid
Suzuki reaction
Phenylboronic acid
Suzuki reaction
Coupling reaction
Aqueous medium
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A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (<1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.
Phenylboronic acid
Coupling reaction
Suzuki reaction
Boronic acid
Aqueous medium
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Abstract A series of new water‐soluble cyclopalladated ferrocenylimines were designed and prepared. They were efficient catalyst for Suzuki coupling reactions of aryl bromides and phenylboronic acid in neat water under ambient atmosphere. Among of these catalysts, the catalyst ( C 2 D ) could be reused for 6 times for the Suzuki coupling reaction of 4‐bromotoluene with phenylboronic acid in EtOH/H 2 O under ambient atmosphere, in which no significant loss activity of C 2 D was observed.
Phenylboronic acid
Suzuki reaction
Coupling reaction
Boronic acid
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A green route for the synthesis of palladium (Pd) nanoparticles (Pd NPs) employing Poplar leaf extract as a reducing and capping agent is described. The as-prepared Pd NPs are spherical with a face centred cubic structure, a particle distribution of 2.2-6.8 nm and an average particle size of 4.2 nm. The application of this catalyst toward homogeneous Suzuki coupling reactions was investigated. The Pd NPs afforded a yield of 98.86% in the Suzuki coupling reaction of 4-bromotoluene with phenylboronic acid using 0.01 mmol% of the catalyst at 60°C for 30 min under an air atmosphere.
Phenylboronic acid
Suzuki reaction
Coupling reaction
Reducing agent
Particle (ecology)
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Abstract A simple and efficient method for Suzuki cross‐coupling of highly substituted and congested 1‐chloro‐2‐nitrobenzene with phenylboronic acid was developed, investigated, and optimized. The reaction conditions comprises a mixture of MeOH and water (4:1) as the reaction medium, readily available and cheap Pd(PPh 3 ) 4 as catalyst, sodium carbonate as base, and microwave heating, which affords a fast reaction rate with good outcomes. The procedure was proven to have high functional group tolerance with phenylboronic acid and for 1‐chloro‐2‐nitrobenzene and thus is a general method for the synthesis of 2‐nitrobiphenyl. The target scaffold, 2‐nitrobiphenyls, was produced in excellent yields with excellent selectivities in all cases.
Phenylboronic acid
Nitrobenzene
Suzuki reaction
Coupling reaction
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Phenylboronic acid
Benzimidazole
Suzuki reaction
Coupling reaction
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A new palladium–Schiff base complex immobilized on iron oxide nanoparticles (γ-Fe2O3-acetamidine-Pd) was synthesized via the reaction of amino-functionalized γ-Fe2O3 with acetamide followed by the reaction with palladium acetate. Characterization of γ-Fe2O3-acetamidine-Pd was carried out by various techniques such as XRD, SEM, HRTEM, FT-IR, TGA, ICP, XPS and elemental analysis. γ-Fe2O3-acetamidine-Pd was successfully applied as a magnetically recyclable catalyst in Heck and Suzuki coupling reactions. By these protocols, aryl halides were coupled with olefins (Heck coupling reaction) and phenylboronic acid (Suzuki coupling reaction) to afford the corresponding products in moderate to high yields. Furthermore, the synthesized catalyst was separated easily by using an external magnet and recycled for five runs without appreciable loss of its catalytic activity.
Phenylboronic acid
Heck Reaction
Suzuki reaction
Coupling reaction
Acetamide
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Transition-metal catalyzed reaction represents an extremely versatile method in organic synthesis. [1] Searching for highly efficient catalysts has been the aim of organic chemists. Palladium catalyzed coupling of aryl halides with arylboronic acids, Suzuki reaction, is one of the most powerful methods for carbon-carbon bond formation. [2] Here we report the high efficiency of cyclopalladated ferrocenylimine 1 for the Suzuki coupling reaction of aryl iodides with phenylboronic acid. Excellent yields and high turnover numbers were obtained under optimized conditions after repeated uses (Schemes 1, 2).……
Phenylboronic acid
Suzuki reaction
Coupling reaction
Organic Synthesis
Aryl halide
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Five 1‐alkyimidazoline (1–5) have been prepared and characterized by conventional spectroscopic methods and elemental analyses. New in situ generated palladium‐imidazoline complexes were tested for catalytic activity in the Suzuki coupling reaction between phenylboronic acid and several aryl chlorides.
Phenylboronic acid
Coupling reaction
Suzuki reaction
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Abstract A series of solvents were examined for the ligand free Pd(II)‐catalyzed Suzuki reaction of 4‐bromotoluene with phenylboronic acid. It was found that the PdCl 2 / i ‐PrOH system could efficiently inhibit the homo‐coupling of phenylboronic acid and give a cross‐coupling product in high yields. The substrates with a wide variety of functional groups were tolerated in the system. A possible mechanism for this system was proposed.
Phenylboronic acid
Suzuki reaction
Coupling reaction
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