Metal Supported on Dendronized Magnetic Nanoparticles:  Highly Selective Hydroformylation Catalysts

Abu‐Reziq, Raed; Alper, Howard; Wang, Dashan; Post, Michael L.

doi:10.1021/ja060140u

Cited by 478 publications

(236 citation statements)

References 62 publications

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“…Moreover, the ability of magnetic nanoparticles to serve efficiently as nano-support for organocatalytic systems has been recently reported [22][23][24][25][26][27][28][29][30][31][32]. We have described the highly selective hydroformylation reaction using rhodium catalysts supported on dendronized magnetic nanoparticles [33]. We have also developed a catalytic system for the chemoselective hydrogenation of α, β-unsaturated aldehydes and alkynes, based on platinum nanoparticles supported on nano-magnetite, Fe 3 O 4 , modified with ionic liquid groups [34].…”

Section: Open Accessmentioning

confidence: 99%

Magnetically Separable Base Catalysts: Heterogeneous Catalysis vs. Quasi-Homogeneous Catalysis

Abu‐Reziq

Alper

2012

Applied Sciences

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Abstract:The synthesis of magnetically separable quasi-homogeneous base catalyst and heterogeneous base catalyst is described. The quasi-homogeneous catalyst is achieved by supporting silane monomers functionalized with different amine groups directly on the surface of magnetite nanoparticles. The heterogeneous catalyst is prepared via a sol-gel process in which silane monomers containing different amine groups are copolymerized with tetraethoxysilane in the presence of magnetite nanoparticles functionalized with ionic liquid moieties. The reactivity of the quasi-homogeneous and the heterogeneous base catalysts is compared in the nitroaldol condensation.

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Section: Open Accessmentioning

confidence: 99%

Magnetically Separable Base Catalysts: Heterogeneous Catalysis vs. Quasi-Homogeneous Catalysis

Abu‐Reziq

Alper

2012

Applied Sciences

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“…in situ removal of water and moisture absorbing materials are the two options [25][26][27], which were often observed with minimum success and inconsistent yields [25][26][27]. Recent mechanism studies had suggested that moisture was not the real problem and the catalysts offering more surface area have proven to be more useful [28][29][30][31]. The use of Fe 3 O 4 @SiO 2 was first of its sort and near doubling of reaction yield is in expected lines considering our similar observation with thiophenes, terpyridine, quinazoline and isoxazole [23].…”

Section: Synthesis Of 2-amino-5-carboethoxy-4-hydroxypyrimidine Withoutmentioning

confidence: 99%

“…The nanomaterial based catalysis is not reported for pyrimidine synthesis and our group has recently reported that Fe 3 O 4 @SiO 2 acts as an inert support in some organic reactions. This inert solid support catalyst was shown to give significantly improved yields for reactions involving ring cyclizations [23,28,29]. The mechanism seems to be intermediate stabilization due to its interaction with silica surface.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Microbicidal Activity of Substituted 1,2,3-Triazoles having Amide and Hydroxy Functionality

Kaushik¹,

Luxmi²

2017

Asian J. Chem.

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Pyrimidines and pyridines are choice for modern day medicinal chemistry. Pyrimidine synthons are synthesized form guanidine and different substituted malonates. One of such pyrimidine ring synthon is 2-amino-5-carboethoxy-4-hydroxy pyrimidine. The commercially deployed synthesis involved a mixture of KOH and guanidine carbonate and gradual temperature controlled addition of diethylethoxy methylene melonate giving a yellow precipitate. The precipitate is cooled to around 5 °C and recrystallized from ethanol-water mixture. Though purity is never an issue in this popular process, yields are very low (70-75 %). The GC analysis of reaction mixture indicated that almost starting material was left unreacted and the first yellow precipitate formation is the rate determining step. We report silica functionalized magnetic particles as material support for synthesis of 2-amino-5carboethoxy-4-hydroxy pyrimidine. The cyclization reaction yields are reported to be enhanced due to presence of "near-homogeneous" nanomaterial catalyst. The prominent catalyst of interest to us is Fe3O4@SiO2 of 40 nm size. The particles are produced by modified Stober process giving consistent yields and coating of SiO2. The structural characterization is performed with SEM, TEM, IR and the data are consistent across multiple batches. The use of 40 nm size Fe3O4@SiO2 enabled higher yields of cyclization step in synthesis of 2-amino-5-carboethoxy-4-hydroxy pyrimidine. The mechanism of catalysis is stabilization of hetero atoms on the acidic silica surface and hence formation of pyrimidine. The study with different sized nanoparticles has indicated 40 nm size seems to be optimum and ability of catalysis is reduced as the size of nanoparticles has increased. The reaction performed at different batch sizes has indicated that 5 % (w/v) catalyst is optimal in the reaction. This process modification has far reaching applications in medicinal chemistry and bulk drug synthesis.

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“…Thus, novel supports that ensure both good recyclability and catalytic activity are still desirable. MNP have recently appeared as a new type of catalyst support because of their easy preparation and functionalization, large surface area ratio, facile separation via magnetic force as well as low toxicity and price (Yoon et al, 2003;Stevens et al, 2005;Lee et al, 2006;Abu-Reziq et al, 2006;Luo et al, 2008). These features have made MNP a promising alternate of porous/mesoporous catalyst supports.…”

Section: Ionic Liquids Immobilized On Mnp and Their Applications In Omentioning

confidence: 99%

DBU Derived Ionic Liquids and Their Application in Organic Synthetic Reactions

Chen¹,

Ying²

2011

Ionic Liquids: Applications and Perspectives

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Metal Supported on Dendronized Magnetic Nanoparticles: Highly Selective Hydroformylation Catalysts

Cited by 478 publications

References 62 publications

Magnetically Separable Base Catalysts: Heterogeneous Catalysis vs. Quasi-Homogeneous Catalysis

Magnetically Separable Base Catalysts: Heterogeneous Catalysis vs. Quasi-Homogeneous Catalysis

Synthesis and Microbicidal Activity of Substituted 1,2,3-Triazoles having Amide and Hydroxy Functionality

DBU Derived Ionic Liquids and Their Application in Organic Synthetic Reactions

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