Three-dimensional amine-terminated ionic liquid functionalized graphene/Pd composite aerogel as highly efficient and recyclable catalyst for the Suzuki cross-coupling reactions

Huang, Yu Ping; Wei, Qiuli; Wang, Yuanyuan; Dai, Liyi

doi:10.1016/j.carbon.2018.04.068

Cited by 58 publications

(31 citation statements)

References 46 publications

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“…Aer the process of oxidation, the mixture was repeatedly washed with an HCl solution and water (1 : 10) by repeated centrifugation. 8 Then, the product was puried by dialysis for one week using a dialysis membrane with a molecular weight cut off of 8000-10 000 g mol À1 ; this removed the remaining acid and the residual salts. To obtained smaller sheets, graphite oxide was exfoliated by an ultrasonic cell crusher.…”

Section: Preparation Of Graphene Oxide (Go)mentioning

confidence: 99%

“…This means that the distance between Pd atoms increases as the particle size decreases. 8,51 By tting the Pd (1 1 1) peak via the Scherrer equation, the average size of the Pd nanoparticles supported on the undoped (catalyst-0 (A)) and N-doped graphene (catalyst-3 (D)) composites was calculated to be about 7.5 nm and 3.2 nm, respectively. These results are consistent with those of the TEM statistical particle size analysis.…”

Section: Catalyst Characterizationmentioning

confidence: 99%

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Three-dimensional N-doped graphene aerogel-supported Pd nanoparticles as efficient catalysts for solvent-free oxidation of benzyl alcohol

et al. 2019

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Section: Preparation Of Graphene Oxide (Go)mentioning

confidence: 99%

Section: Catalyst Characterizationmentioning

confidence: 99%

Three-dimensional N-doped graphene aerogel-supported Pd nanoparticles as efficient catalysts for solvent-free oxidation of benzyl alcohol

et al. 2019

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“…We have found that K 2 CO 3 exerts most effectively for the Suzuki cross‐coupling reaction, superior to Na 2 CO 3 , KOH, CsCO 3 and other bases in our previous work . Therefore, we adopted K 2 CO 3 as base for the Suzuki cross‐coupling reaction.…”

Section: General Experimental Detailsmentioning

confidence: 96%

“…This would cause a series of problems such as hindered mass transfer of the catalyst and agglomeration of the active components . Our precious research has introduced ionic liquids to synthesize 3D self‐assembled modified Pd/graphene materials . A nucleophilic ring‐opening reaction between the epoxy groups of GO and the amine groups of 1‐(3‐aminopropyl)‐3‐methylimidazolium bromide (IL‐NH 2 ) is easily occurred to form the IL‐modified graphene.…”

Section: Introductionmentioning

confidence: 99%

Pd‐Cu alloy nanoparticle supported on amine‐terminated ionic liquid functional 3D graphene and its application on Suzuki cross‐coupling reaction

Huang

Wang

et al. 2019

Applied Organom Chemis

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Well distributed Pd-Cu bimetallic alloy nanoparticles supported on amineterminated ionic liquid functional three-dimensional graphene (3D IL-rGO/ Pd-Cu) as an efficient catalyst for Suzuki cross-coupling reaction has been prepared via a facile synthetic method. The introduction of IL-NH 2 cations on the surface of graphene sheets can effectively avoid the re-deposition of graphene sheets, allowing the catalyst to be reused up to 10 cycles. The addition of Cu not only saves cost but also ensures high catalytic efficiency. It is worthy to note that the catalyst 3D IL-rGO/Pd 2.5 Cu 2.5 can efficiently catalyze the Suzuki cross-coupling reaction with the yield up to 100% in 0.25 h, almost one-fold higher than that by the pristine IL-rGO/Pd 2.5 catalyst (52%). The Powder X-Ray Diffraction (XRD), combining energy dispersive X-ray spectroscopy (EDS) mapping results confirm the existence and distribution of Pd and Cu in the bimetallic nanoparticles. The transmission electron microscopy (TEM) reveals the nanoparticle size with an average diameter of 3.0 ± 0.5 nm. X-ray photoelectron spectroscopy (XPS) analysis proved the presence of electron transfer from Cu to Pd upon alloying. Such alloying-induced electronic modification of Pd-Cu alloy and 3D ionic liquid functional graphene with large specific surface area both accounted for the catalytic enhancement.

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“…Despite a lot of articles claiming that heterogeneous catalysts are just a reservoir of active species as depicted above, some authors, even very recently [69,70], consider that the solid material is the only true catalyst for the reaction. Their conclusions are supported by different analyses, either of the Pd content in the solution or by split-tests, poisoning tests or other ways to try to identify the active species.…”

Section: Putative Heterogeneous Catalystsmentioning

confidence: 99%

About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

2019

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A critical review of conclusions about the putative heterogeneous mechanism in the Suzuki-Miyaura coupling by supported Pd solids is reported. In the first section, the turnover frequencies (TOF) of 20 well-established homogeneous catalysts are shown to be in the range 200 to 1,000,000,000 h − 1 . The evidences used to prove a heterogeneous mechanism are discussed and another interpretation is proposed, hypothesizing that only the leached species are responsible for the catalytic reaction, even at ppb levels. Considering more than 40 published catalytic systems for which liquid phase Pd content have been reported, activities have been computed based on leached Pd concentrations and are shown to be in the range TOF 150 to 70,000,000 h − 1 . Such values are compatible with those found for the well-established homogeneous catalysts which questions the validity of the conclusions raised by many papers about the heterogeneous (solid) nature of Suzuki-Miyaura catalysis. Last, a tentative methodology is proposed which involves the rational use of well-known tests (hot-filtration test, mercury test…) to help to discriminate between homogeneous and heterogeneous mechanisms.

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Three-dimensional amine-terminated ionic liquid functionalized graphene/Pd composite aerogel as highly efficient and recyclable catalyst for the Suzuki cross-coupling reactions

Cited by 58 publications

References 46 publications

Three-dimensional N-doped graphene aerogel-supported Pd nanoparticles as efficient catalysts for solvent-free oxidation of benzyl alcohol

Three-dimensional N-doped graphene aerogel-supported Pd nanoparticles as efficient catalysts for solvent-free oxidation of benzyl alcohol

Pd‐Cu alloy nanoparticle supported on amine‐terminated ionic liquid functional 3D graphene and its application on Suzuki cross‐coupling reaction

About Solid Phase vs. Liquid Phase in Suzuki-Miyaura Reaction

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