A Magnetic Biomimetic Nanocatalyst for Cleaving Phosphoester and Carboxylic Ester Bonds under Mild Conditions

Zheng, Yan; Duanmu, Chuansong; Gao, Yong

doi:10.1021/ol061098a

Cited by 50 publications

(33 citation statements)

References 12 publications

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“…The various types of organic reactions using the MNPs-supported catalysts that have emerged recently include C-C coupling reactions [17][18][19][20][21][22][23][24], hydroformylation [25,26], hydrogenation [27][28][29][30][31][32][33][34][35], C-N coupling reaction [36,37], oxidation [38][39][40][41][42][43], cleavage of allyl esters and ethers (deallylation catalyst) [44], enantioselective acylation [45], multicomponents Aza-Sakurai reaction [46], the Paal-Knorr reaction [47], CO 2 cycloaddition reactions [48], asymmetric hydrosilylation of ketones [49], and esterification [50]. Other reports of MNPs-supported catalysts include O-Alkylation reaction [51], halogen exchange reaction [52], polymerization reactions [53], enzymes for carboxylate resolution [54], amino acids for ester hydrolysis [55], organic amine catalysts promoting Knoevenagel [56], one-pot reaction cascades [57], and the various acidcatalyzed reactions (deprotection reaction of benzaldehyde dimethylacetal) [58]. Concerning the Suzuki coupling reactions, palladium complexes...…”

Section: Introductionmentioning

confidence: 99%

Fe3O4 Nanoparticles-Supported Palladium-Bipyridine Complex: Effective Catalyst for Suzuki Coupling Reaction

Zhang

Wei

2010

Catal Lett

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Fe 3 O 4 nanoparticles-supported palladium-2, 2 0 -bipyridine complex was synthesized and used as catalyst for Suzuki coupling reactions between different aryl iodides and bromides with phenyl boronic acid under mild conditions. This catalyst can be separated magnetically. However, due to the aggregation of catalyst with the increase in reaction times, the activity dropped dramatically from[99% for the first time use to 45% for the fourth time use and then kept constant subsequently.

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Section: Introductionmentioning

confidence: 99%

Fe3O4 Nanoparticles-Supported Palladium-Bipyridine Complex: Effective Catalyst for Suzuki Coupling Reaction

Zhang

Wei

2010

Catal Lett

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“…25 Key to the successful application of MNPs is the surface functionalization. There are two general surface modification approaches taken: (1) Molecules containing functional groups such as carboxylic acids or phosphoric acids are attached through noncovalent reversible absorption on MNPs; 22,28,29 although this approach is conceptually simple, the presence of a functional group does not guarantee that a ligand will remain bound to the surface of a nanoparticle at various stages of surface modification and during application. In fact, the loss of catalytic activities of MNP supported catalyst was attributed to the dissociation of catalysts from MNP surface.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of magnetic nanoparticles with organic molecules: Loading level determination and evaluation of linker length effect on immobilization

Balasubramanian

Huang

2007

Chirality

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A general method is introduced to immobilize organic molecules on magnetic nanoparticles through silanization reactions and determine the maximum loading level by UV-vis spectroscopy. Loading levels of 1.5 x 10(-3) mol per gram of nanoparticle were obtained with structurally diverse compounds such as rhodamine B and glucosamine. The length of the linker did not have a significant effect on loading as comparable maximum amounts of rhodamine B were immobilized on magnetic nanoparticles regardless of the linker length. Interestingly, rhodamine B derivatives lost conjugation during synthetic manipulations due to reversible spiroisobenzofuran formation. Full regeneration of conjugation was found to be slow with rhodamine B attached on magnetic nanoparticles. The results obtained from these studies will be useful for studying surface functionalization of MNPs in general.

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“…Major methods in synthesis of organic molecule-immobilized magnetically retrievable catalysts (MRCs) focus on traditional strategies, in which organic catalysts or ligands are bonded onto the surface of magnetic nanoparticles (MNPs) or SiO 2 -supported MNPs. Earlier research in supporting of organic molecule onto Fe 2 O 3 MNPs was reported by Gao group [43] at 2006. As shown in Scheme 1, they used dopamine as a linker for immobilization of two amino acid residues (Asp and His residues, which have a carboxylate group and an imidazole molecule on side chains, respectively).…”

Section: Organic Catalysts Immobilized On Magnetic Nanoparticlesmentioning

confidence: 95%

Recent advances in catalysts immobilized on magnetic nanoparticles

Mokhtary

2016

J IRAN CHEM SOC

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2]. Furthermore, enhancing the percentages of exposed highly reactive facets, at nanoscale, does improve the efficiency of materials in various applications such as photocatalysis and dye-sensitized solar cells [3]. By presenting individual properties, nanoparticles can become a kind of structure unit, in other words, "artificial atoms" to conduct a new type of materials which have difficult in estimating collective properties [4]. Through green nanotechnology, we can get contrivable nanomaterial that contains unique characters which bulk materials never have [5]. This means that we are creating materials with good catalytic activity, stability and more selectivity via changing their forms, sizes and morphologies [6]. Applications of nanoparticles in catalytic reactions are because as size decreases, the surface area-to-volume ratio increases, which enhanced interaction between the reactant and the catalyst, which are needed for high catalytic efficiencies [7]. Unsupported nanoparticles are often less stable, and usually coagulation is inevitable during the catalytic reactions [8]. To generate stable nanoparticles with good activity, stabilizing the surface is required. Protection has been performed by the addition of polymers or longchain alkyl surfactants with polar functional groups that attached to the nanoparticle surface via covalent or electrostatic interactions [9, 10]. Alternatively, nanoparticles have been immobilized or grafted onto inorganic supports to improve their stabilization and recycling ability [12]. Progress in the discovery of new support materials for the heterogenization of homogeneous catalysts has been periodically reviewed [13]. In this article, the green catalytic processes and recent advances in organic transformations catalyzed by magnetically retrievable catalysts (MRCs) are highlighted. Prior to this, methods for the synthesis of catalysts immobilized on magnetic nanoparticles will be addressed briefly.Abstract Unsupported nanoparticles are often less stable, and usually coagulation is unavoidable during the catalytic reactions. To generate stable nanoparticles with good activity, stabilizing the surface is required. Protection has been performed by the addition of polymers or long-chain alkyl surfactants with polar functional groups that attached to the nanoparticle surface via covalent or electrostatic interactions. Alternatively, nanoparticles have been immobilized or grafted onto inorganic supports to improve their stabilization and recycling ability. In this article, the green catalytic processes and recent advances in organic transformations catalyzed by magnetically retrievable catalysts are reviewed. Prior to this, methods for the synthesis of catalysts immobilized on magnetic nanoparticles are addressed briefly.

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A Magnetic Biomimetic Nanocatalyst for Cleaving Phosphoester and Carboxylic Ester Bonds under Mild Conditions

Cited by 50 publications

References 12 publications

Fe3O4 Nanoparticles-Supported Palladium-Bipyridine Complex: Effective Catalyst for Suzuki Coupling Reaction

Fe3O4 Nanoparticles-Supported Palladium-Bipyridine Complex: Effective Catalyst for Suzuki Coupling Reaction

Functionalization of magnetic nanoparticles with organic molecules: Loading level determination and evaluation of linker length effect on immobilization

Recent advances in catalysts immobilized on magnetic nanoparticles

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