Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

Gómez‐Martínez, Melania; Baeza, Alejandro; Alonso, Diego A.

doi:10.3390/catal7030094

Cited by 24 publications

(11 citation statements)

References 80 publications

(108 reference statements)

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“…The chemical bonding states of PPOU and Fe-PPOU were characterized via XPS. The N 1s high-resolution XPS spectrum of PPOU (Figure 2d) presented three N signals corresponding to oximido N, amido N, and pyridyl N at 400.4, 399.6, and 398.5 eV, respectively [51][52][53]. The peak area ratio of oximido N to pyridyl N was about 2:1.…”

Section: Resultsmentioning

confidence: 99%

Supertough spontaneously self-healing polymer based on septuple dynamic bonds integrated in one chemical group

et al. 2021

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The development of spontaneously self-healing materials with excellent mechanical properties remains a formidable challenge despite the extensive interest in such materials. This is because the self-healing and mechanical properties of a material are usually optimized via contradictory routes. The present study demonstrated a supertough spontaneously self-healing polymer, Fe-(2,6-diacetylpyridine dioxime)-urethane-based polyurethane (Fe-PPOU) based on septuple dynamic bonds integrated in one chemical group. A synergistic effect was induced by the presence of multiple dynamic crosslinking points, which comprised the integrated dynamic interactions, and the hidden lengths of the folded polymeric chains in Fe-PPOU. Thus, the mechanical and self-healing properties of the polymer were simultaneously optimized. Fe-PPOU demonstrated the highest reported toughness (139.8 MJ m−3 ) among all the room-temperature spontaneously self-healing polymers with a nearly 100% healing rate. Fe-PPOU exhibited instant (30 s) self-healing to reach a strength of 1.6 MPa that was higher than the original strength of numerous recently reported self-healing polymers.

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Section: Resultsmentioning

confidence: 99%

Supertough spontaneously self-healing polymer based on septuple dynamic bonds integrated in one chemical group

et al. 2021

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“…In addition, a high surface-to-weight ratio, low mass density, and accessibility of differently modified centres make it possible to select GO for catalytic applications. The successful use of Pd/GO in the Suzuki-Miyaura reaction has been reported [12][13][14][15][16][17][18][19][20][21][22][23][24][25]. Not only high conversion but also good catalyst recyclability have been achieved.…”

Section: Introductionmentioning

confidence: 98%

Palladium Nanoparticles Supported on Graphene Oxide as Catalysts for the Synthesis of Diarylketones

et al. 2019

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Three palladium catalysts supported on graphene oxide (GO) and on its composite with TiO2 (GO-TiO2) were prepared and characterized. The presence of Pd NPs of different diameters (4–89 nm) and size distributions was evidenced by TEM measurements. GO-supported palladium efficiently catalysed the carbonylative coupling of iodobenzenes with aryl boronic acids forming relevant diarylketones at 1 atm CO. The highest activity and recyclability were obtained for Pd/GO-TiO2. The emission behaviour of Pd/GO and Pd/GO-TiO2 catalysts indicated structural changes occurring during the catalytic reaction.

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“…The Suzuki–Miyaura cross-coupling reaction between halo derivatives and boronic acids catalyzed by Pd(0) compounds, which was awarded with the Nobel laureate in 2010, , is one of the most reliable, efficient, and practical methodology for the formation of C–C bonds since its first report in 1979. − In particular, the reaction is a versatile and powerful methodology, for example, in the construction of biaryl compounds and the substitution and modification of aromatic and heteroaromatic moieties. − In this context, the Suzuki–Miyaura reaction is used in many research fields because it permits the efficient discovery, development, and synthesis of pharmaceutical and chemical compounds, of different kinds of engineering materials (liquid crystals, polymers, molecular wires, etc. ), coordination chemistry materials, supramolecular chemistry, and diverse functional materials. ,− …”

Section: Introductionmentioning

confidence: 99%

Porous Organic Polymers Containing Active Metal Centers for Suzuki–Miyaura Heterocoupling Reactions

Esteban

Ferrer

Ania

et al. 2020

ACS Appl. Mater. Interfaces

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A new generation of confined palladium(II) catalysts covalently attached inside of porous organic polymers (POPs) has been attained. The synthetic approach employed was straightforward, and no prerequisite of making any modification of the precursor polymer was needed. First off, POP-based catalytic supports were obtained by reacting one symmetric trifunctional aromatic monomer (1,3,5-triphenylbenzene) with two ketones having electronwithdrawing groups (4,5-diazafluoren-9-one, DAFO, and isatin) in superacidic media. The homopolymers and copolymers were made using stoichiometric ratios between the functional groups and they were obtained with quantitative yields after an optimization of reaction conditions. Moreover, the number of chelating groups (bipyridine moieties) available to bind Pd(II) ions in the catalyst supports was modified using different DAFO/isatin ratios. The resulting amorphous polymers and copolymers showed high thermal stability, above 500 ºC, and moderate-high specific surface areas (from 760 to 935 m 2 g -1 ), with a high microporosity contribution (from 64% to 77%). Next, POP-supported Pd(II) catalyst were obtained by simple immersion of the catalyst supports in a palladium (II) acetate solution, observing that the metal content was similar to that theoretically expected according to the amount of the bipyridine groups. The catalytic activity of these heterogeneous catalysts was explored for the synthesis of biphenyl and terphenyl compounds, via the Suzuki-Miyaura cross-coupling reaction using a green solvent (ethanol/water), low palladium loads and aerobic conditions. The findings showed excellent catalytic activity with quantitative product yields. Additionally, the recyclability of the catalysts was excellent because after 5 cycles of use, by a simple washing with ethanol, the coupling yield was higher than 95%. Finally, the feasibility of these catalysts to be employed in tangible organic reactions was assessed. Thus, the synthesis of a bulky compound, 4-4'-3 dimetoxi-5'-t-butyl-m-terphenylene, which is a precursor of a thermally rearrangement monomer, was scaled-up to 2 g, with high conversion and 96% yield of pure product.

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Graphene Oxide-Supported Oxime Palladacycles as Efficient Catalysts for the Suzuki–Miyaura Cross-Coupling Reaction of Aryl Bromides at Room Temperature under Aqueous Conditions

Cited by 24 publications

References 80 publications

Supertough spontaneously self-healing polymer based on septuple dynamic bonds integrated in one chemical group

Supertough spontaneously self-healing polymer based on septuple dynamic bonds integrated in one chemical group

Palladium Nanoparticles Supported on Graphene Oxide as Catalysts for the Synthesis of Diarylketones

Porous Organic Polymers Containing Active Metal Centers for Suzuki–Miyaura Heterocoupling Reactions

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