Hydroformylation of methyl methacrylate catalyzed by homogeneous and polymer-attached rhodium complexes

Pittman, Charles U.; Honnick, W. D.; Yang, Jinliang

doi:10.1021/jo01292a027

Cited by 49 publications

(25 citation statements)

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“…Um estudo sistemático sobre a hidroformilação do metacrilato de metila catalisado por HRh(CO)(PPh 3 ) 3 e por seus derivados ancorados a matrizes poliméricas, foi realizado há alguns anos atrás 77 . Tendo em conta o fato da regiosseletividade da hidroformilação do metacrilato de metila ser muito sensível às condições de reação, a mesma foi correlacionada com a variação dos seguintes parâmetros: (i) relação Fosfina/Rh, (ii) pressão e relação CO/H 2 , (iii) temperatura, (iv) solvente e ligantes adicionados, (v) emprego de HRh(CO)(PPh 3 ) 3 ancorado em diversos polímeros.…”

Section: Fármacos Diversosunclassified

“…Os sistemas catalíticos ancorados a uma resina estireno-divinilbenzênica são mais seletivos que os correspondentes catalisadores homogêneos na direção do isômero ramificado, quando mantida a mesma relação P/Rh. Por exemplo, uma resina com uma carga de difosfina da ordem de 29% e P/Rh = 3, a 80 o C e 130 atm, fornece 75% de produto ramificado, contra somente 57% obtido com o catalisador homogêneo 77 .…”

Section: Fármacos Diversosunclassified

“…Até o momento, somente o 3-butenoato de etila, foi tomado em consideração 77,82 . A hidroformilação deste éster, já apresentada na primeira parte desta revisão, conduz ao 5-oxopentanoato de etila, utilizado na síntese de produtos naturais como o mircenol, feromônios e prostaglandinas 81 .…”

Section: Esquema 16unclassified

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Contribuições recentes da reação de hidroformilação na síntese de produtos farmacêuticos: parte II

Botteghi¹,

Marchetti²,

Ponte³

1997

Quím. Nova

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Preto-USP-Via do Café s/n-14040-903-Ribeirão Preto-SP Recebido em 19/12/95; aceito em 16/10/96 CURRENT IMPROVEMENT TO THE SYNTHESIS OF PHARMACEUTICALS BY HYDROFOR-MYLATION REACTION. PART II. The hydroformylation reaction represents one of the most important C1-chemistry area in the chemical industry. This catalytic process, which has been developed up to now mainly to the production of commodities chemicals, has shown a remarkable potential for the preparation of several categories of specialty chemicals and in particular pharmaceutical compounds. Arylpropanoic acids, various amines containing aryl groups, and intermediates for the preparation of vitamins, carbocyclic and heterocyclic compounds and many other classes of organic molecules endowed with pharmacological activity are currently accessible in good-to-high yields through hydroformylation of selected olefinic substrates. The asymmetric hydroformylation is going to reach the stage of maturity and hence to contribute in solving many troublesome synthetic problems connected with the preparation of pharmacologically active compounds with very high enantiomeric purity. The present survey emphasizes the usefulness of synthesis gas as a starting material in fine chemistry, which is expected to be important for industry.

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Section: Fármacos Diversosunclassified

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Contribuições recentes da reação de hidroformilação na síntese de produtos farmacêuticos: parte II

Botteghi¹,

Marchetti²,

Ponte³

1997

Quím. Nova

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“…Therefore, most of the studies focused on the development of polymerbased catalysts imply that the phosphorus-containing fragments are fi xed in the polymer structure and the obtained materials are treated with noble metal complexes thereafter. Rhodim catalysts based on a modifi ed styrene and divinylbenzene copolymer were among the fi rst to be obtained and studied [39][40][41][42][43][44][45][46][47][48][49]. The copolymer was chloromethylated [39] or brominated [40] by aromatic fragments and then subjected to the action of LiPPh 2 in THF in order to obtain phosphine-containing polymers, onto which rhodium was later applied.…”

Section: Doi: 101134/s0965544121010011mentioning

confidence: 99%

Polymeric Heterogeneous Catalysts in the Hydroformylation of Unsaturated Compounds

et al. 2020

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This review deals with heterogeneous hydroformylation catalysts, specifically metal complexes fixed in an organic polymer structure. It describes the main catalyst synthesis methods, provides data on hydroformylation of unsaturated compounds (including asymmetric hydroformylation), and shows how those compounds can be used. The special focus is on the systematization of data on heterogeneous catalysts developed on the basis of porous organic polymers. Due to their porous structure, resistance to organic media and the high concentration of heteroatoms they contain, these materials can be considered promising for developing highly active, selective and stable heterogeneous catalysts for hydroformylation of unsaturated compounds, particularly higher linear olefins.

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“…polymer support phase (17,33); and local differences in the chelating ligand to complex molar ratios (30,39,40). The role of substrate transport is the most easily identified and quantified of the above effects; however it has only been treated in detail in a limited number situations (11,12,16,17).…”

mentioning

confidence: 99%

The Role of Substrate Transport in Catalyst Activity

Ekerdt

1986

ACS Symposium Series

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This paper addresses the general subject of substrate transport in polymer-immobilized catalyst systems. The equations needed to interpret reaction rate data for polymer systems are developed and their applicability is discussed. The effects of experimental variables on observed reaction rates in the presence of substrate transport limitations are discussed. A simple method for estimating substrate diffusion coefficients is presented. Methods for testing reaction rate data to determine if substrate transport is affecting the observed reaction rates are developed and the limitations of these methods are discussed.Finally, examples of recent studies are reviewed and discussed within the framework of the mathematical formalism to demonstrate application of the formalism and to show that carefully designed experiments are required to establish the presence of substrate limitations.Numerous studies have appeared in the literature in which transition metal complexes, immobilized on functionalized-polymers, or in which sulfonated resins have been used as catalysts. Polystyrene is the most common polymer support and has been used in the gelform and macroreticular forms. Review articles on "immobilized catalysts" have presented the advantages and disadvantages of immobilizing the catalytic site (1-8). The primary motivation is to "hetrogenize" a homogenous catalyst and thereby avoid costly separations of the catalyst from the reaction mixture and, in the case of acids, to minimize contact of the corrosive catalyst with the reactor vessel.Polymer-immobilized catalysts cannot be considered to be heterogeneous in the same sense that zeolites or metals supported on porous oxides are heterogeneous. These latter catalysts involve well defined rigid support structures in which the active sites reside at specific locations within the solid particle. The

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Hydroformylation of methyl methacrylate catalyzed by homogeneous and polymer-attached rhodium complexes

Cited by 49 publications

References 1 publication

Contribuições recentes da reação de hidroformilação na síntese de produtos farmacêuticos: parte II

Contribuições recentes da reação de hidroformilação na síntese de produtos farmacêuticos: parte II

Polymeric Heterogeneous Catalysts in the Hydroformylation of Unsaturated Compounds

The Role of Substrate Transport in Catalyst Activity

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