Non covalent immobilization of pyrene-tagged ruthenium complexes onto graphene surfaces for recycling in olefin metathesis reactions

Nasrallah, Houssein; Germain, Stéphane; Queval, Pierre; Bouvier, C.; Mauduit, Marc; Crévisy, Christophe; Schulz, Emmanuelle

doi:10.1016/j.molcata.2016.10.004

Cited by 17 publications

(12 citation statements)

References 46 publications

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“…Several Hoveyda‐type ruthenium complexes, bearing pyrene tags on the NHC ligand and/or on the benzylidene moiety, were synthesized and tested in olefin metathesis reactions . The evaluation of the catalytic activity was assessed in the ring‐closure metathesis of diethyl diallylmalonate.…”

Section: Graphene‐ Graphene Oxide‐ and Reduced Graphene Oxide‐based mentioning

confidence: 99%

Modified Nanocarbons for Catalysis

2018

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Nanocarbons represent useful scaffolds in the preparation of last generation nanostructured catalysts, and their chemical functionalization through covalent or non‐covalent modification is becoming an important tool for introducing well‐distributed anchoring points and, in the meantime, could be the first step toward the assembling of hybrid nanostructured materials with a hierarchical order. In this Review are reported synthesis and catalytic applications of chemically modified nanocarbons such as fullerene, carbon nanotubes, graphene, nanohorns and nanodiamonds in organocatalytic and metal‐based (metal nanoparticles, organometallic complexes) reactions, covering major chemical reactions encompassing, the oxidation of alcohols, aldehydes, olefins, and silanes, hydrogenation reactions of aldehydes, ketones, and alkenes, dehydrogenative coupling of silanes, C−C coupling reactions, epoxidation of alkenes, CO2 fixation into cyclic carbonates, and asymmetric reactions, among others.

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Section: Graphene‐ Graphene Oxide‐ and Reduced Graphene Oxide‐based mentioning

confidence: 99%

Modified Nanocarbons for Catalysis

2018

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“…Especially in hybrid catalysts prepared by immobilization of well-defined Mo and Ru carbenes, these properties have proved particularly useful. Although some Ru carbenes have also been immobilized on other materials such as Metal-Organic Framework MOF [84], graphene [85,86], glass, wool, and paper [87], the data reported so far show that SBA-15 is the most promising support for effective, stable, and widely applicable catalysts.…”

Section: Discussionmentioning

confidence: 99%

SBA-15 as a Support for Effective Olefin Metathesis Catalysts

Balcar

Čejka

2019

Catalysts

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Olefin metathesis is the catalytic transformation of olefinic substrates, finding a wide range of applications in organic synthesis. The mesoporous molecular sieve Santa Barbara Amorphous (SBA-15) has proven to be an excellent support for metathesis catalysts thanks to its regular mesoporous structure, high BET area, and large pore volume. A survey of catalysts consisting of (i) molybdenum and tungsten oxides on SBA-15, and (ii) molybdenum and ruthenium organometallic complexes (Schrock and Grubbs-type carbenes) on SBA-15 is provided together with their characterization and catalytic performance in various metathesis reactions. The comparison with catalysts based on other supports demonstrates the high quality of the mesoporous molecular sieve SBA-15 as an advanced catalyst support.

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“…The non‐covalent interaction between pyrene and rGO is based on van der Waals interactions (π‐stacking) and control with thermodynamic factors. Some of the valuable immobilization methods developed recently are those involving π–π stacking using graphene, carbon nanotubes, nanoparticles or polymers as supports …”

Section: Introductionmentioning

confidence: 99%

Catalytic activity and facile recovery of a cyclometalated N‐heterocyclic carbene palladium(II) complex immobilized by non‐covalent interactions on reduced graphene oxide

Karami

Ramezanpour

Zakariazadeh

et al. 2019

Applied Organom Chemis

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The growing concern about the potentially adverse effects of the production of chemical compounds on the sustainable development of the environment has led to a great deal of efforts to search for low-cost and environmentally friendly catalytic systems. A pyrene-tagged N-heterocyclic carbene palladacycle complex ([Pd{(C,N)C 6 H 4 CH 2 NH(Et)}(Imd-P)Br]) was prepared by reacting imidazolium salt with dimer ([Pd 2 {(C,N)C 6 H 4 CH 2 NH(Et)} 2 (μ-OAc) 2 ]). Then, it was immobilized onto the surface of reduced graphene oxide (rGO) via π-π stacking forces. The hybrid compound ((NHC)Pd-rGO) was made in a one-step process. Various techniques were employed to characterize the compound. In addition, computational studies were used to verify the interaction between the Pd complex and rGO. The catalytic activity of the molecular complex and hybrid material was evaluated in both Suzuki-Miyaura cross-coupling reactions and reduction of p-nitrophenol to p-aminophenol. The catalytic activity of the hybrid material was enhanced in comparison with the corresponding homogeneous analogue. Thus, rGO seems to play a significant role in catalytic activity. Hot filtration experiments show the heterogeneous nature of the catalyst resulting from the strong interaction between pyrene and graphene. The hybrid (NHC)Pd-rGO material could be recycled up to six times with no decrease in catalytic activity.

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Non covalent immobilization of pyrene-tagged ruthenium complexes onto graphene surfaces for recycling in olefin metathesis reactions

Cited by 17 publications

References 46 publications

Modified Nanocarbons for Catalysis

Modified Nanocarbons for Catalysis

SBA-15 as a Support for Effective Olefin Metathesis Catalysts

Catalytic activity and facile recovery of a cyclometalated N‐heterocyclic carbene palladium(II) complex immobilized by non‐covalent interactions on reduced graphene oxide

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