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1.
An efficient and simple ligand derived from phthalandione was used for palladium catalyzed Suzuki coupling reaction in water/ethanol (V/V = 2/1) under aerobic conditions. The reaction exhibited a high catalytic efficiency even with lower Pd loading (0.002 mol %). In this work, the catalyst could be successfully used in coupling reaction between various aryl halides with phenylboronic acid in excellent yields with high turnover number (TON) (the maximal TON was up to 49,000 for the reaction of bromobenzene with phenylboronic acid). Moreover, this new ligand had been elucidated by 1H NMR, 13C NMR and X-ray crystal diffraction. 相似文献
2.
Heng-Shan Wang Ying-Chun Wang Ying-Ming Pan Zhen-Feng Chen 《Tetrahedron letters》2008,49(16):2634-2637
An efficient method for palladium-catalyzed Suzuki cross-coupling reaction with simultaneous reduction of nitro- to amino-group has been developed. This method allows nitro-substituted aryl halides to readily react with arylboronic acids, to afford aryl substituted aniline in low to excellent yields. The reaction was catalyzed by Pd(OAc)2 (3 mol %) at 150 °C under atmospheric pressure in the presence of K2CO3 (3 equiv) in DMF/H2O (5/1). 相似文献
3.
Wei Wang Rongliang Wang Fan Wu Boshun Wan 《Reaction Kinetics and Catalysis Letters》2005,85(2):277-282
Summary A Ni-promoted ligand free palladium catalyst system for Suzuki coupling of aryl bromides has been developed in high efficiency under mild reaction conditions. It was obtained in situ by introducing NiCl2 to PdCl2/PVP using a parallel high-throughput screening technique. A wide range of aryl bromides bearing a variety of functional groups was evaluated. 相似文献
4.
A new palladium incorporated carbonaceous catalyst Pd@CCSO3HNH2 was synthesized by introducing palladium on glucose derived carbocatalyst. The catalyst was well characterized and was used for the Suzuki coupling of phenyl boronic acid with different aryl halides under aqueous conditions. This green methodology represents a ligand free, cost-effective and operationally convenient method for the synthesis of a variety of biaryl’s under the conditions that are tolerant for a broad range of functional groups with good to excellent yields. Moreover, the catalyst could be easily recycled and reused at least five times without any significant loss of its catalytic activity. 相似文献
5.
Fluorinated compounds have attracted considerable attention in pharmaceuticals, agrochemicals and material science due to their unique physical properties. This paper reports an efficient and environmentally benign protocol for the Suzuki reaction of aryl halides with fluorinated arylboronic acids over a thermoregulated ligand/palladium catalyst using water as sole medium, affording a variety of fluorinated biaryls, including fluorinated liquid crystals, in excellent yields. The catalyst could be recycled four times with high activity. The active catalyst was proved to be a palladium/ligand complex via a mercury-poisoning test. 相似文献
6.
Kin Hong Liew Wan Zurina Samad Norazzizi Nordin Poh Lee Loh Joon Ching Juan Mohd Ambar Yarmo Badrul Hisham Yahay Rahimi M.Yusop 《催化学报》2015,(5):771-777
A new heterogeneous catalyst composed of Pd nanoparticles immobilized within a HypoG el resin has been prepared in the absence of any ligands using an extensive cross-linking method.This newly developed nanocatalyst was characterized by N_2 adsorption-desorption,X-ray diffraction(XRD),transmission electron microscopy(TEM),scanning electron microscopy(SEM),energy dispersive X-ray(EDX),Fourier transform infrared spectroscopy and inductively coupled plasma-mass spectrometer(ICP-MS)techniques.TEM and XRD results revealed that the Pd nanoparticles were well dispersed with diameters in the range of 4–12 nm,and an average size of about 8 nm.The cross-linked Pd catalyst demonstrated excellent catalytic activity towards the synthesis of a series of biaryl compounds by the reaction of various aryl halides(e.g.,bromides andiodides)with phenylboronic acid in the presence of tetrabutylammonium bromide.ICP-MS analysis indicated that there was only 0.25%weight loss of Pd(0.55±0.02 ppm)from the supported catalyst after the first cycle reaction.Furthermore,the catalyst showed excellent reusability(up to five uses)with consistently high levels of catalytic activity following its recovery by filtration. 相似文献
7.
Kin Hong Liew Wan Zurina Samad Norazzizi Nordin Poh Lee Loh Joon Ching Juan Mohd Ambar Yarmo Badrul Hisham Yahaya Rahimi M. Yusop 《催化学报》2015,(5)
A new heterogeneous catalyst composed of Pd nanoparticles immobilized within a HypoGel resin has been prepared in the absence of any ligands using an extensive cross-linking method. This new-ly develop... 相似文献
8.
Sodium 2-(2-pyridin-3-ylethylamino)ethyl sulfonate: an efficient ligand and base for palladium-catalyzed Suzuki reaction in aqueous media 总被引:1,自引:0,他引:1
PdCl2, N-donor ligand and base mediated Suzuki coupling reaction of aryl halides and arylboronic acid in water are described. The corresponding Suzuki products were obtained in good to excellent yields. 相似文献
9.
Song-Se Yi 《Tetrahedron letters》2007,48(38):6771-6775
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. 相似文献
10.
《Tetrahedron》2014,70(21):3471-3477
A new simple Pd(memantine)2Cl2 complex was synthesized and characterized by 1H NMR, 13C NMR and X-ray single crystal structure determination. The Suzuki–Miyaura reaction of aryl bromides catalyzed by Pd(memantine)2Cl2 complex was investigated in air with different temperature. The high turnover numbers of 650,000 have been obtained in the reaction of 4-bromonitrobenzene with phenylboronic acid at 80 °C. At room temperature, the complex also showed high activity for Suzuki–Miyaura cross-coupling reaction of aryl bromides with a wide range of functional groups under air, and the turnover number of up to 99,000 was achieved. The catalytic system also gives good yields toward the reaction of several heteroaryl bromides with thiophenylboronic acid. 相似文献
11.
The ortho-metallated complex [Pd(μ-Cl){κ2(C,C)-[C6H4(PPh2CHC(O)C6H4-Ph-4)}]2 (2a) was prepared by refluxing of Pd(OAc)2 and {(Ph)3PCHCOC6H4-Ph-4} (PhBPPY) of in CH2Cl2 followed by addition of an excess of KCl in MeOH Complex (2a) reacts with triphenylphosphine to give the mononuclear derivative [Pd(Cl)(PhC6H4COCHPPh2C6H4)(PPh3)] (3a) whose crystal structure has been determined by single crystal X-ray diffraction. The Suzuki reactions of aryl bromides and chlorides of varying electron density using complex (3a) as an efficient catalyst were performed, giving the cross-coupling products in good to excellent yields. 相似文献
12.
13.
Trideep Rajale Shikha SharmaDaniel A. Stroud Daniel K. Unruh Emily MiaouKimberly Lai David M. Birney 《Tetrahedron letters》2014
An efficient Pd-catalyzed Suzuki cross-coupling reaction of sterically crowded 4-chlorocoumarin derivatives with air- and moisture-stable potassium organotrifluoroborates is developed. This methodology has been used to generate a series of novel alkyl, aryl, and vinyl substituted coumarin derivatives in good to excellent yields. The twisted conformation of the vinyl groups in the X-ray crystal structures of (2-oxo-4-vinyl-2H-chromen-3-yl)methyl acetate (2) and (2-oxo-4-vinyl-2H-chromen-3-yl)methyl 2,2,2-trichloroacetimidate (3), along with the atropisomerism of 3-(hydroxymethyl)-4-(2-methoxyphenyl)-2H-chromen-2-one (1d), are evidence of the steric crowding in these adducts. 相似文献
14.
A variety of aryl nitriles were prepared in excellent yields from the palladium acetate catalyzed coupling of aryl halides with Zn(CN)2 using polymer-supported triphenyl phosphine as the ligand and dimethylformamide as solvent under microwave irradiation conditions. 相似文献
15.
The efficiency of various palladium salts as catalysts in the Suzuki cross-coupling reaction, and the influence of the base and temperature used on its conversion, were studied. The use of PdCl2 supported on hydrotalcite as catalyst in the presence of potassium carbonate as base was found to provide the best results. Reaction temperatures above 90 °C ensured conversion levels on a par with those for many homogeneous catalysts. 相似文献
16.
Mohammad Joshaghani Marzieh Daryanavard Ezzat Rafiee Jianliang Xiao 《Tetrahedron letters》2007,48(11):2025-2027
The biphenyl-based phosphine, P(o-C6H4C6H4Me)Ph2, is a moderately bulky and electron-rich phosphine, which has been successfully applied to the palladium catalyzed Suzuki coupling of activated and deactivated aryl halides as well as bromoarylphosphines and bromoarylphosphine oxides, with low catalyst loading and good to excellent conversions and turnovers. 相似文献
17.
Several water-soluble cyclopalladated complexes with five- or six-membered rings have been prepared as air-stable solids from Schiff base ligands bearing an N-phenyl sulfonate groups. Cyclopalladated complexes with six-membered rings show high catalytic efficiency for the Suzuki reactions of aryl bromides with phenylboronic acid in aqueous solvents under mild conditions. Palladium complex 1 can be used for five reaction cycles in high conversions for the Suzuki reactions in neat water without additives. The catalytic process for the Suzuki couplings is proved by TEM analysis to proceed on Pd(0) nanoparticles. Surfactant-protected palladium nanoparticles present lower activities and poorer recyclability for the coupling reactions than those generated in situ without additives. 相似文献
18.
In this work, ortho‐palladated complexes [Pd(µ‐Cl)(C6H4CH2 NRR′‐κ2‐C,N)]2 and [Pd(C6H4CH2NH2‐2‐C,N)Cl(Y)] were tested in the Suzuki–Miyaura cross‐coupling reaction. Cyclopalladated Pd(II) complexes as thermally stable catalysts can activate aryl bromides and chlorides. These complexes were active and efficient catalysts for the Suzuki–Miyaura reaction of aryl bromides and even less reactive aryl chlorides. The cross‐coupled products of a variety of aryl bromides and aryl chloride with phenylboronic acid in methanol as solvent at 60 °C were produced in excellent yields. Copyright © 2010 John Wiley & Sons, Ltd. 相似文献
19.
Sangita Karanjit Masaya Kashihara Atsushi Nakayama Lok Kumar Shrestha Katsuhiko Ariga Kosuke Namba 《Tetrahedron》2018,74(9):948-954
A palladium(0) nanocluster supported on hydrotalcite has been prepared and tested for the Suzuki coupling reaction. The prepared catalyst showed very efficient catalytic activity for cross coupling of iodo- and bromoarenes under very mild reaction conditions, affording >90% yield. Under the optimized reaction conditions, chloroarenenes also showed very good reactivity. Transmission electron microscopic imaging data showed the formation of very small Pd(0)-nanoclusters (d = 2.2 ± 0.5 nm) well dispersed on the support, which enhanced the activity and stability of the catalyst for the Suzuki cross-coupling reaction. This catalytic system offers an easy method of preparation with good activity and reusability up to five cycles. 相似文献
20.
R. Rama Suresh 《Tetrahedron letters》2009,50(44):6004-265
An economic and novel ligand, cyclodiphosphazane [ClPN(t-Bu)]2 (1), was introduced in the palladium-catalyzed amination of unactivated aryl halides. The catalyst allows for the amination of aryl chlorides and bromides with secondary cyclic amines and anilines in good yields. 相似文献