Green synthesis of fluorinated biaryl derivatives via thermoregulated ligand/palladium-catalyzed Suzuki reaction

Liu, Ning; Li, Chun; Zhang, Jin

doi:10.1016/j.jorganchem.2011.04.007

Cited by 39 publications

(20 citation statements)

References 55 publications

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“…In all cases, these TOF values were much higher than in the case of similar systems based on alumina and Pd nanoparticles [14] or mesoporous silica and palladium nanoparticles [12]. In addition, they are in the same range, if not somewhat higher, than those described for homogeneous systems based on palladium complexes used for the preparation of fluorinated biaryls [29][30][31][32][33][34][35]. The reactions using the other two boronic acids, 4-carboxyphenylboronic acid, and 4-vinylphenylboronic acid, showed less conversion of the halide.…”

Section: Influence Of the Fluorinated Aryl Bromidementioning

confidence: 65%

“…In addition, they are in the same range, if not somewhat higher, than those described for homogeneous systems based on palladium complexes used for the preparation of fluorinated biaryls [29][30][31][32][33][34][35].…”

Section: Determination Of the Optimal Conditions And Influence Of Difmentioning

confidence: 67%

“…Almost all of these reports described homogeneous systems based on Pd-complexes as catalysts [29][30][31][32][33][34][35], while only one study was carried out using Pd nanoparticles [36]. Therefore, we report here the synthesis and characterization of palladium nanoparticles supported onto commercial graphene modified with COOH groups and the study of the application of this composite material in Suzuki-Miyaura C-C coupling heterogeneous catalytic reactions in the formation of fluorinated biphenyls.…”

Section: Introductionmentioning

confidence: 99%

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Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

et al. 2017

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Heterogeneous recyclable catalysts in Suzuki-Miyaura C-C coupling reactions are of great interest in green chemistry as reusable alternatives to homogeneous Pd complexes. Considering the interesting properties of fluorinated compounds for the pharmaceutical industry, as precursors of novel materials, and also as components of liquid crystalline media, this present study describes the preparation of different fluorinated biphenyl derivatives by Suzuki-Miyaura coupling reactions catalyzed by a heterogeneous system (G-COOH-Pd-10) based on Pd nanoparticles supported onto COOH-modified graphene. The catalytic activity of the hybrid material G-COOH-Pd-10 has been tested in Suzuki-Miyaura C-C coupling reactions observing excellent versatility and good conversion rates in the reactions of phenylboronic acid, 4-vinylphenylboronic acid, 4-carboxyphenylboronic acid, and 4-fluorophenylboronic acid with 1-bromo-4-fluorobenzene. In addition, the influence of the arylbromide has been studied by carrying out reactions of 4-fluorophenylboronic acid with 1-bromo-2-fluorobenzene, 1-bromo-3-fluorobenzene, 1-bromo-4-fluorobenzene, 2-bromo-5-fluorotoluene, and 2-bromo-4-fluorotoluene. Finally, catalyst recyclability tests show a good degree of reusability of the system based on G-COOH-Pd-10 as the decrease in catalytic activity after five consecutive catalytic cycles in the reaction of 1-bromo-4-fluorobenzene with 4-florophenylboronic acid at 48 hours of reaction is lower than 8% while in the case of reactions at three hours the recyclability of the systems is much lower.

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Section: Influence Of the Fluorinated Aryl Bromidementioning

confidence: 65%

Section: Determination Of the Optimal Conditions And Influence Of Difmentioning

confidence: 67%

Section: Introductionmentioning

confidence: 99%

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Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

et al. 2017

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“…Palladium-catalyzed C-C bond construction [1,2,3,4,5,6,7,8] that makes use of readily available substrates and proceeds with high chemoselectivity has established itself as a flexible synthetic protocol for obtaining substituted arene and heteroarene derivatives [9,10,11,12,13] (e.g., symmetrical or unsymmetrical biaryls) [14]. This synthesis approach has revolutionized the production of advanced materials [15,16,17,18], pharmaceuticals [19,20,21], agrochemicals [21,22], liquid crystals [23], and natural or biologically active compounds [24,25,26,27,28], etc.…”

Section: Introductionmentioning

confidence: 99%

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Ding

Yan

et al. 2018

Molecules

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An easy access to a series of previously unreported heterodinuclear Pd-Ln compounds, Pd-bpydc-La, Pd-bpydc-Ce and Pd-bpydc-Nd (bpydc = 2,2′-bipyridine-5,5′-dicarboxylate) has been developed. The Pd-Ln hybrid networks were effectively applied as catalysts in Suzuki–Miyaura C-C cross-coupling reactions of 4-bromoanisole and 4-bromobenzonitrile with phenylboronic acid, under mild conditions. A systematic investigation revealed Pd-bpydc-Nd as the most active catalyst. In all cases, reaction yields varied with the base, catalyst loading and substantially augmented with temperature (from 30 to 60 °C). Substituent effects were operative when changing from 4-bromoanisole to 4-bromobenzonitrile. The key role played by the lanthanides, aromatic substrate and base, in modulating the Pd-catalytic cycle has been highlighted. Importantly, the new catalysts proved to be stable in air and vs. functionalities and are quite efficient in Suzuki–Miyaura carbon-carbon bond formation conducted in protic solvents.

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“…Up to this point, numerous thermomorphic catalytic systems have been reported. [12][13][14][15] Unfortunately, while biphasic conditions facilitate catalyst separation and reuse, multiple phases introduce kinetic barriers and mass transfer limitations. Moreover, the traditional thermoregulated phase-transfer catalysis suffers from requirement of organic solvents or special palladium catalysts such as palladacycles.…”

Section: Introductionmentioning

confidence: 99%

Thermoregulated Aqueous Biphasic Catalysis of Sonogashira Reactions

Zhao

Liu

2015

Aust. J. Chem.

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Green synthesis of fluorinated biaryl derivatives via thermoregulated ligand/palladium-catalyzed Suzuki reaction

Cited by 39 publications

References 55 publications

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives

Efficient Suzuki–Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds

Thermoregulated Aqueous Biphasic Catalysis of Sonogashira Reactions

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