Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by palladium complexes bridged with <i>N</i>,<i>N</i>‐ligands over functionalized silica

Fan, Guozhi; Li, Tao; Li, Guangxing

doi:10.1002/aoc.1062

Cited by 21 publications

(8 citation statements)

References 26 publications

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“…An aliquot of 1.81 g (5.6 mmol) of (1-methyl-2-pyridylmethyl)[(triethoxylsilyl)propyl]amine 1, which was synthesized according to the literatures, 36,37 was added to the suspension of MCM-41, followed by refluxation of the resulting solution for 20 h under N 2 . The product was recovered by filtration, washed thoroughly with distilled water and ethanol, and dried at 60…”

Section: Catalyst Preparationmentioning

confidence: 99%

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Fan

Cheng

Zhu

et al. 2007

Applied Organom Chemis

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Palladium chloride was grafted to amino-functionalized MCM-41 to prepare heterogeneous catalysts. XRD, N 2 adsorption-desorption isotherms, IR, 13 C and 29 Si cross-polarization magic-angle spinning NMR spectroscopy and XPS techniques were employed to characterize the catalytic materials. The heterogeneous palladium catalyst exhibited excellent catalytic activity for the Heck vinylation of iodobenzene with methyl acrylate, giving 92% yield of methyl cinnamate in the presence of Nmethylpyrrolidone (NMP) and triethylamine (Et 3 N). The stability of the heterogeneous catalyst was also studied in detail. The catalytic tests showed that the palladium leaching correlated to solvent, base and palladium loading. The heterogeneous catalyst exhibited excellent stability towards loss of activity and palladium leaching was not observed during six recycles in the presence of toluene and Na 2 CO 3 .

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Section: Catalyst Preparationmentioning

confidence: 99%

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Fan

Cheng

Zhu

et al. 2007

Applied Organom Chemis

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“…However, the former reaction is thermodynamically unfavorable (K P = 3 9 10 -4 at 453 K) and suffers from low yield and selectivity to DPC even at elevated temperatures [8]. The latter is usually catalyzed by noble metal Pd catalyst but the catalytic activity is relatively poor [9,10]. It is still necessary, therefore, to develop other more efficient and green routes for the synthesis of DPC.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diphenyl Carbonate from Phenol and Carbon Dioxide in the Presence of Carbon Tetrachloride and Zinc Chloride

et al. 2009

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Diphenyl carbonate (DPC) was synthesized from phenol and dense phase CO 2 in the presence of CCl 4 and K 2 CO 3 using different catalysts of ZnCl 2 , ZnBr 2 , Lewis acid ionic liquids including 1-butyl-3-methylimidazolium chloride (BMIMCl) and bromide (BMIMBr). It was found that K 2 CO 3 was not required, ZnCl 2 and ZnBr 2 were similar in the catalytic performance, and the use of BMIMCl and BMIMBr was not effective for the production of DPC. For the reactions with ZnCl 2 in CCl 4 , the effects of such reaction variables as temperature, CO 2 pressure, the amount of ZnCl 2 , and the volume of CCl 4 were studied in detail. It was shown that the pressure was less influential while a larger amount of ZnCl 2 , a smaller volume of CCl 4 , and a low temperature of around 100°C were beneficial for the synthesis of DPC. On the basis of the results obtained, possible reaction mechanisms were discussed.

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“…All experiments were performed under a dinitrogen atmosphere unless otherwise noted. The ligands, PQ H , PQ Me and PQ Ph were prepared by the method reported previously. , The starting complexes, [PtCl 2 (EtCN) 2 ], [PtCl 2 (PhCN) 2 ] and [PdCl 2 (PhCN) 2 ] were prepared according to the literature methods.…”

Section: Methodsmentioning

confidence: 99%

Sterically Demanding 8-(Diphenylphosphino)quinoline Complexes of Group 10 Metal(II): Synthesis, Crystal Structures, and Properties in Solution

2020

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Several series of platinum(II), palladium(II), and nickel(II) complexes bearing 8-(diphenylphosphino)quinoline (PQH) or its 2-methyl or 2-phenyl derivatives (PQMe or PQPh) were synthesized, and their crystal structures and behaviors in solution were investigated. Most of the complexes [M(PQR)2]X2 (MII = PtII, PdII, or NiII; R = H, Me or Ph; X = monoanionic ions) characterized in this study have an approximately square-planar coordination geometry with two bidentate P,N-chelating or monodentate P-donating quinolylphosphine ligands in the cis(P,P) configuration. A large steric requirement from the Me or Ph substituent introduced at the 2-position of the quinoline ring gives the resulting complexes severe distortion. The PtII and PdII complex cations maintained the square-planar coordination geometry, but the MII center was displaced from the chelating ligand plane. This bending of the chelate coordination makes the M–N(quinoline) bond weaker, as demonstrated by the longer M–N bonds. In accord with the bond weakening, the partial dissociation of the PQH or PQMe chelates by substitution with halide anions were observed using UV–vis spectroscopy and X-ray crystallography. In contrast, the PQPh complexes were stable in solution toward the addition of halide anions; the intramolecular π–π stacking interaction between the coordinating quinolyl and the 2-substituted phenyl rings protects the MII center from nucleophilic attack. In the corresponding NiII complexes, the steric congestion arising from the mutually cis-positioned PQR ligands resulted in a large tetrahedral distortion around the NiII center. However, the intramolecular π–π stacking interaction was still effective in the PQPh complex, and this interaction can explain some unusual robustness and electrochemical properties of the NiII–PQPh complex.

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Oxidative carbonylation of phenol to diphenyl carbonate catalyzed by palladium complexes bridged with N,N‐ligands over functionalized silica

Cited by 21 publications

References 26 publications

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Palladium chloride anchored on organic functionalized MCM‐41 as a catalyst for the Heck reaction

Synthesis of Diphenyl Carbonate from Phenol and Carbon Dioxide in the Presence of Carbon Tetrachloride and Zinc Chloride

Sterically Demanding 8-(Diphenylphosphino)quinoline Complexes of Group 10 Metal(II): Synthesis, Crystal Structures, and Properties in Solution

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