Pd-grafted porous metal–organic framework material as an efficient and reusable heterogeneous catalyst for C–C coupling reactions in water

Roy, Anupam Singha; Mondal, John; Banerjee, Biplab; Mondal, Paramita; Bhaumik, Asim; Islam, Sk. Manirul

doi:10.1016/j.apcata.2013.10.017

Cited by 138 publications

(71 citation statements)

References 69 publications

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“…[44][45][46] In order to confirm the homogeneity/heterogeneity of Pd(0)-TBA@biochar, coupling of iodobenzene with phenylboronic acid in the presence of PVP was examined. Polyvinylpyridine (PVP) poisoning and mercury poisoning tests are often employed for extinguishing solution-phase catalysis.…”

Section: Leaching Of Catalystmentioning

confidence: 99%

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Moradi

Hajjami

Valizadeh-kakhki

2019

Applied Organom Chemis

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Biochar is a stable and carbon-rich solid which has a high density of carbonyl, hydroxyl and carboxylic acid functional groups on its surface. In this work, the surface of biochar nanoparticles (BNPs) was modified with 3-choloropropyltrimtoxysilane and further 2-(thiophen-2-yl)-1H-benzo[d]imidazole was anchored on its surface. Then, palladium nanoparticles were fabricated on the surface of the modified BNPs and further the catalytic application was studied as recyclable biocatalyst in carbon-carbon coupling reactions such as Suzuki-Miyaura and Heck-Mizoroki cross-coupling reactions. The structure of the catalyst was characterized using scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, X-ray diffraction and atomic absorption spectroscopy. The catalyst can be reused several times without a decrease in its catalytic efficiency.In addition to the several advantages reported, application of biochar as catalyst support for the first time is a major novelty of the present work. 1 H NMR (400 MHz, CDCl 3 ): δ H = 10.09 (s, 1H), 7.99-7.97 (d, J = 8 Hz, 2H), 7.79-7.77 (d, J = 8 Hz, 2H), 7.68-7.66 (d, J = 8 Hz, 2H), 7.53-7.49 (t, J = 8 Hz, 2H), 7.47-7.43 (t, J = 8 Hz, 1H) ppm. 2.5.4 | [1,1′-Biphenyl]-3-carbaldehyde 1 H NMR (400 MHz, CDCl 3 ): δ H = 10.12 (s, 1H), 8.40 (s, 1H), 8.15-8.14 (d, J = 2 Hz, 1H), 7.91-7.87 (td, J = 4 Hz, J = 2 Hz, 1H), 7.68-7.65 (m, 2H), 7.62-7.57 (dd, J = 12 Hz, J = 4 Hz, 1H), 7.53-7.49 (t, J = 8 Hz, 2H), 7.45-7.43 (m, 1H) ppm. 2.5.5 | 3,4-Difluoro-1,1′-biphenyl 1 H NMR (400 MHz, CDCl 3 ): δ H = 7.56-7.54 (d, J = 8 Hz, 2H), 7.49-7.45 (t, J = 8 Hz, 2H), 7.44-7.38 (m, 2H), 7.34-7.31 (m,1H), 7.28-7.21 (m, 1H) ppm. 2.5.6 | Butyl 3-(4-methylphenyl)acrylate 1 H NMR (400 MHz, CDCl 3 ): δ H = 7.70-7.66 (d, J = 16 Hz, 1H), 7.46-7.44 (d, J = 8 Hz, 2H), 7.22-7.20 (d, J = 8 Hz, 2H), 6.44-6.40 (d, J = 16 Hz, 1H), 4.25-4.21 (t, J = 8 Hz, 2H), 2.39 (s, 3H), 1.75-1.68 (quint, J = 8 Hz, 2H), 1.51-1.42 (sextet, J = 8 Hz, 2H), 1.01-0.97 (t, J = 8 Hz, 3H) ppm. | Butyl 3-(4-methoxyphenyl)acrylate

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Section: Leaching Of Catalystmentioning

confidence: 99%

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Moradi

Hajjami

Valizadeh-kakhki

2019

Applied Organom Chemis

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“…[22,23] Combining some special physical properties of both organic and inorganic porous materials, MOF-based structures exhibit several advantages as compared to conventional materials. [27][28][29] A variety of MOFs have been employed as catalysts or catalyst supports for many organic reactions, ranging from carbon-carbon [30][31][32][33] to carbon-heteroatom forming transformations. [27][28][29] A variety of MOFs have been employed as catalysts or catalyst supports for many organic reactions, ranging from carbon-carbon [30][31][32][33] to carbon-heteroatom forming transformations.…”

Section: Introductionmentioning

confidence: 99%

Direct Oxidative Amidation between N,N‐dimethylanilines and Anhydrides Using Metal‐Organic Framework [Cu₂(EDB)₂(BPY)] as an Efficient Heterogeneous Catalyst

Dang

Nguyen

et al. 2014

ChemPlusChem

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A crystalline porous metal‐organic framework [Cu2(EDB)2(BPY)] was synthesized and used as a heterogeneous catalyst for the direct oxidative amidation between N,N‐dimethylanilines and anhydrides to form tertiary amides as the principal products. The [Cu2(EDB)2(BPY)] exhibited similar activity as compared to that of [Cu2(BDC)2(BPY)], [Cu2(BDC)2(DABCO)], MOF‐143, and other common homogeneous salt catalysts. The optimal reaction conditions employed were [Cu2(EDB)2(BPY)] (10 % mol), TBHP (2 equiv), pyridine (1 equiv) in CH3CN at 80 °C over 2 h. The Cu2(EDB)2(BPY) could be separated from the reaction mixture by filtration, and could be recovered and reused several times without a significant degradation in catalytic activity and selectivity. Furthermore, generality of the optimal conditions was confirmed by employing various N,N‐dimethylaniline and anhydride derivatives.

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“…Such transformations include Suzuki-Myaura [94][95][96][97], Sonogashira [97,98], Ulmann [94], and Heck [99] reactions. Compared to other metal M a n u s c r i p t 15 A wide range of applications, including chemical threat detection, medical diagnostics, food/drink quality control, explosives and pollutants detection, requires sensors that detect specific molecules or elements with high selectivity, sensitivity, and speed of analysis [125][126][127].…”

Section: Carbon-carbon Couplingmentioning

confidence: 99%

Application of metal and metal oxide nanoparticles@MOFs

Falcaro

Riccò

Yazdi

et al. 2016

Coordination Chemistry Reviews

520

244

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Pd-grafted porous metal–organic framework material as an efficient and reusable heterogeneous catalyst for C–C coupling reactions in water

Cited by 138 publications

References 69 publications

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Direct Oxidative Amidation between N,N‐dimethylanilines and Anhydrides Using Metal‐Organic Framework [Cu₂(EDB)₂(BPY)] as an Efficient Heterogeneous Catalyst

Application of metal and metal oxide nanoparticles@MOFs

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Pd-grafted porous metal–organic framework material as an efficient and reusable heterogeneous catalyst for C–C coupling reactions in water

Cited by 138 publications

References 69 publications

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Biochar as heterogeneous support for immobilization of Pd as efficient and reusable biocatalyst in C–C coupling reactions

Direct Oxidative Amidation between N,N‐dimethylanilines and Anhydrides Using Metal‐Organic Framework [Cu2(EDB)2(BPY)] as an Efficient Heterogeneous Catalyst

Application of metal and metal oxide nanoparticles@MOFs

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Product

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Direct Oxidative Amidation between N,N‐dimethylanilines and Anhydrides Using Metal‐Organic Framework [Cu₂(EDB)₂(BPY)] as an Efficient Heterogeneous Catalyst