Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction

Wang, Xiaoxia; Hu, Peibo; Xue, Fengjun; Wei, Yuping

doi:10.1016/j.carbpol.2014.08.030

Cited by 87 publications

(28 citation statements)

References 50 publications

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“…The obtained FTIR of ILBr‐Al‐MCM‐41 shows a band at 2958 cm −1 that is attributed to aliphatic C‐H in the structure. The appeared band at 1567 cm −1 is related to C=N of imidazolium rings . Observation of these new band along with the characteristic bands of Al‐MCM‐41 could somewhat confirm the immobilization of the ILBr on Al‐MCM‐41.…”

Section: Resultsmentioning

confidence: 71%

Organic–inorganic hybrid of anchored dicationic ionic liquid on Al‐MCM‐41‐phosphovanadomolybdate toward selective oxidation of benzene to phenol

Taheri

Ghiaci

Moheb

et al. 2019

Applied Organom Chemis

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A phosphovanadomolybdate hybridized with an anchored dicationic ionic liquid on Al-MCM-41 was prepared through the anion exchange and characterized by 1 H and 13 C NMR, FTIR, UV-Vis, XRD, XPS, TGA, TEM, FESEM, ICP-OES and BET techniques. The obtained data demonstrated that the composite is a porous material with the high surface area and also having a large pore volume which are 405 m 2 g −1 and 0.616 cm 3 g −1 respectively. The prepared composite has shown an acceptable catalytic activity for converting benzene selectively to phenol with hydrogen peroxide as eco-friendly oxidant.Under the optimized reaction conditions, the hybrid catalyst resulted in phenol yield of 14.8% with 100% selectivity and a TOF value of 20.0 h −1 . The catalyst also revealed a desired recovery and reusability. The efficient performance of the composite is related to the textural and polyoxometalate properties.

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Section: Resultsmentioning

confidence: 71%

Organic–inorganic hybrid of anchored dicationic ionic liquid on Al‐MCM‐41‐phosphovanadomolybdate toward selective oxidation of benzene to phenol

Taheri

Ghiaci

Moheb

et al. 2019

Applied Organom Chemis

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“…Various supports including polymers, Fe 3 O 4 nanoparticles, silicates, zeolites and carbon materials such as graphene oxide (GO) and reduced graphene oxide (rGO) have been used in the immobilization of metal complexes. Pd(II) complexes of N‐heterocyclic carbenes (NHCs) have been reported as immobilized homogeneous catalysts for C&bond;C coupling reactions on various suitable supports . The formation of a covalent bond between an appropriate support and a complex is definitely the most extensively applied approach for the immobilization of a homogeneous catalyst.…”

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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“…8 The modification of cellulose to anchoring palladium species for catalytic application in Suzuki-Miyaura reactions is also reported in different ways, such as cellulose-aluminum oxide composite modified with organic groups, 9 modified carboxymethyl cellulose 19 and functionalized cellulose. 20 In the last decade, the selective oxidation of the primary alcohols of carbohydrates structure into carboxylates using n-oxil-2,2,6,6-tetramethylpiperidine (TEMPO) catalytic oxidation has been reported. [21][22][23][24] This process has also been applied to cellulose leading to new cellulose derivative.…”

Section: Introductionmentioning

confidence: 99%

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

Martins

Santos

Rodrigues

et al. 2017

J. Braz. Chem. Soc.

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This work shows the modification of microcrystalline cellulose by the selective oxidation of primary hydroxyl groups to carboxylate groups by a 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-mediated system and its application as a heterogeneous ligand by ionic exchange with catalytic metals ions such as palladium, nickel and copper. Afterwards is described the application of the synthesized material as catalyst in coupling reactions such as Suzuki-Miyaura coupling and C−O bond formation reaction in different conditions, which are of great importance for the synthesis of drugs, natural products and new materials such as dendrimers, liquid crystals and polymers with magnetic and optical properties. The carboxyl cellulose matrix shows to have superior catalytic results as a ligand for all coupling reactions. Can be also highlighted the affinity of the carboxyl cellulose ligand in polar solvents such as water and alcohols and its application in mild conditions.

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Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction

Cited by 87 publications

References 50 publications

Organic–inorganic hybrid of anchored dicationic ionic liquid on Al‐MCM‐41‐phosphovanadomolybdate toward selective oxidation of benzene to phenol

Organic–inorganic hybrid of anchored dicationic ionic liquid on Al‐MCM‐41‐phosphovanadomolybdate toward selective oxidation of benzene to phenol

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

Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C−O Bond Formation Reaction

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