Suzuki Cross-coupling Reaction In Water Research Articles

Isinglass–palladium as collagen peptide–metal complex: a highly efficient heterogeneous biocatalyst for Suzuki cross-coupling reaction in water

The class of bio-nanocatalysts (BNCs) is an evolving innovation that synergistically assimilates advanced nanotechnology with biotechnology. BNCs promote green processes due to their low consumption of chemicals and the absence of toxic by-products. Isinglass (IG), from the Dutch huizenblaas (sturgeon bladder), containing approximately 98% protein collagen, is used to support the immobilization of palladium (Pd) nanoparticles. This process leads to Pd/IG composite, a new class of heterogeneous collagen peptides–metal BNCs that exhibit high catalytic activity and reusability for ligand-free Suzuki coupling reaction in water. Additionally, these BNCs are obviously active in the cross-coupling reaction between acid chloride and arylboronic acid, producing a high yield of the desired ketones. The synthesized BNCs are well-characterized by Fourier transform infrared spectroscopy, field emission scanning electron microscopy, X-ray powder diffraction, X-ray photoelectron spectroscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma, and transmission electron microscopy.

Heterogeneous Suzuki cross-coupling reaction in water catalyzed by palladium nanoparticles supported on individual calcium carbonate plates derived from mussel shell particle

A new palladium nanoparticles catalyst supported on individual calcium carbonate plates (Pd/ICCP) is made from Asian green mussel shells and used as heterogeneous catalyst in Suzuki cross coupling reaction. The reduction of palladium (II) generates palladium (0) nanoparticles which can embed on individual calcium carbonate plates (ICCP) to give Pd/ICCP. The prepared Pd/ICCP catalyst is characterized by scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDX), indicating an entire dispersion of palladium onto the surface of individual calcium carbonate plates. Furthermore, palladium content in the prepared Pd/ICCP catalyst is determined by inductively coupled plasma optical emission spectroscopy (ICP-OES). The optimized study is investigated in Suzuki cross-coupling reaction between 4-iodoanisole and phenylboronic acid. It reveals that using potassium carbonate in mixed solvent of EtOH: H2O (3:2) in the presence of 2 mol% of Pd/ICCP give 4-methoxybiphenyl in 90% isolated yield at 40 °C. Moreover, in the presence of cetyltrimethylammonium bromide (CTAB) as phase transfer agent, the reaction can perform wwwwwwwwwin water as a sole solvent to give the product in excellent yield under the same condition.

Microwave-assisted aqueous Suzuki coupling reactions catalyzed by ionic palladium(II) complexes

Suzuki coupling is one of the most powerful methods for the synthesis of biaryls. We have prepared and characterized a series of unsymmetrical sulfonated water-soluble Pd(II)-pyridyl imine complexes and investigated them as catalysts for the Suzuki cross-coupling reaction in water under microwave irradiation. The compounds proved to be effective catalysts.

Diethanol amine-functionalized polymer-supported palladium (0) complex as catalyst for Suzuki cross-coupling reaction in water

Diethanol amine-functionalized polymer-supported palladium (0) complex as catalyst for Suzuki cross-coupling reaction in water was synthesized and characterized. The catalyst exhibits excellent catalytic activity and stability in the Suzuki cross-coupling reaction. Various aryl bromides were coupled with aryl boronic acids in water, under air, and in the presence of 0.5 mol % of the catalyst to afford corresponding cross-coupled products in high yields at 100°C. Furthermore, the heterogeneous catalyst can be readily recovered by simple filtration and reused for several times only with a slight decrease in its activity. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

Chitosan- g-mPEG-supported palladium (0) catalyst for Suzuki cross-coupling reaction in water

A chitosan- g-mTEG (methoxy triethylene glycol)- or mPEG (methoxy polyethylene glycol)-supported palladium (0) catalyst was prepared for the Suzuki cross-coupling reaction in water. The catalyst showed excellent catalytic activity in the Suzuki cross-coupling reaction without additional phase transfer reagents due to the enhanced solubility of the organic substrate by PEG grafting. In addition, the catalyst could be reused up to five times with the catalytic activity being recovered easily after simple manipulations.

Fluorous silica gel-supported perfluoro-tagged palladium nanoparticles catalyze Suzuki cross-coupling reaction in water

The Suzuki cross-coupling reactions using perfluoro-tagged palladium nanoparticles on fluorous silica gel (FSG) as catalyst, K2CO3 as base and TBAB as additive in H2O affording the corresponding biphenyls in moderate to high yields have been described. The catalyst can be recovered by simple filtration and reused several times with slight decrease in activity.

"Greening Up" the Suzuki Reaction

This article describes the rapid, green synthesis of a biaryl compound (4-phenylphenol) via a Pd(0)-catalyzed Suzuki cross-coupling reaction in water. Mild reaction conditions and operational simplicity makes this experiment especially amenable to both mid- and upper-level undergraduates. The methodology exposes students to purely aqueous microscale organic reactivity and showcases topical research in the milieu of an industrially applicable process.

Chitosan-supported palladium(0) catalyst for microwave-prompted Suzuki cross-coupling reaction in water

A chitosan-supported palladium (Pd) (0) catalyst was prepared by simple adsorption of palladium(II) ion onto chitosan beads and a subsequent reduction process. To maintain mechanical stability, the chitosan-supported palladium(0) catalyst was cross-linked with either glutaraldehyde or diglycidyl ether polyethylene glycol. The catalysts were utilized for the Suzuki cross-coupling reaction in water. The catalyst, in the presence of a tetrabutylammonium bromide (TBAB) additive, showed excellent catalytic activity in microwave-prompted Suzuki cross-coupling reactions using various aryl halides and boronic acids. In addition, the catalyst was successfully reused up to five times without significant loss of catalytic activity.

Recyclable and highly active cationic 2,2′-bipyridyl palladium(II) catalyst for Suzuki cross-coupling reaction in water

A water-soluble and air-stable palladium(II)/cationic 2,2′-bipyridyl catalyst is proven to be a recyclable and extremely active catalyst for Suzuki reaction in aqueous and aerobic conditions. The conveniently prepared catalyst showed little loss in the catalytic process of the coupling between 4-bromoacetophenone and phenylboronic acid after five cycles. For the reactions of aryl chlorides, biaryls were formed in high yields under refluxing temperature in the presence of TBAB.

Amphiphilic polymer supported N-heterocyclic carbene palladium complex for Suzuki cross-coupling reaction in water

We synthesized amphiphilic polymer-supported N-heterocyclic carbene (NHC) precursor resins by loading polyethylene glycol (PEG) containing imidazolium groups on Merrifield resin. These PS–PEG–NHC precursor resins were compatible with water and readily formed a stable complex with palladium. These PS–PEG–NHC–Pd catalysts showed excellent catalytic activity for Suzuki cross-coupling reactions of various aryl iodides and bromides with phenylboronic acid in water than the previously described polystyrene based catalysts. In addition, the PS–PEG–NHC–Pd catalysts continued to provide excellent catalytic activity in Suzuki cross-coupling reactions after five consecutive recycles.

Glucosamine-based phosphines. Efficient ligands in the Suzuki cross-coupling reaction in water

Coupling of protected or non-protected d-glucosamine with o- or p-(diphenylphosphino)benzoic acid generates carbohydrate-substituted phosphines in quite good yields. The catalytic performance of these new neutral ligands is demonstrated in the Suzuki cross-coupling reaction. The polyhydroxy phosphines are more active than the peracetylated phosphines, and the process tolerates electron-rich as well as electron-poor substituents. Excellent turnovers are observed, and the catalyst can be recycled.