Hydrogenation of diene compounds using ruthenium-based catalysts

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Hydrogenation of diene compounds using ruthenium-based catalysts

Popis výsledku v původním jazyce

Hydrogenation of dienes is an important chemical transformation in various fields such as organic synthesis, pharmacochemistry, and industrial chemistry. Selective hydrogenation of conjugated diene compounds is a challenging task. The hydrogenation may be brought about by either 1,2-addition or 1,4-addition. It is well known that the positions of the double bond and functional groups can significantly affect the properties of the product. For these reasons, it is crucial to find a suitable regio-and stereoselective catalytic complex to perform the hydrogenation step. It should be noted that the ratio of products of 1,2-and 1,4-addition, as well as the proportion of Z-and E-isomers, depends on the thermodynamic stability of intermediates and final compounds, the presence of substituents on C=C bonds, the configuration of C=C bonds and also on the properties of the catalyst. The presented review considers the main homogeneous and heterogeneous catalysts based on ruthenium that are used for the hydrogenation of dienes and compounds with a conjugated diene system. Hydrogenation in the presence of supported ruthenium catalysts (Ru/C, Ru/Al2O3) takes place with low selectivity, the 1,4-addition of hydrogen to double C=C bonds do not occur and products of 1,2-addition and saturated compounds are mainly formed. Homogeneous Ru-based catalysts are in most cases highly active and the major product is formed mainly by 1,4-addition. The stereoselectivity of the reaction is significantly dependent on the structure of the catalyst and the type of organic ligands present in the structure. The catalytic performance of ruthenium complexes containing phosphine ligands was studied in the regioselective hydrogenation of dienoic acids. Complexes catalyze the 1,4-addition with moderate regioand stereoselectivity. Ruthenium complexes containing the ligand 1,2,3,4,5-pentamethylcyclopentadienyl (Cp*) in the structure were also applied to perform the hydrogenation of diene compounds. It was found that the presence of the Cp* ligand in the complex structure has a positive effect on both the stability and activity of Ru complexes compared to other ligands. Ruthenium half-sandwich complexes [Cp*Ru (diene compound)]+ were used as catalysts for the hydrogenation of diene compounds. These reactions show high regioselectivity to 1,4-addition products and 100% stereoselectivity to products with Z-configuration of the double bond. © 2023 Nova Science Publishers, Inc.

Název v anglickém jazyce

Hydrogenation of diene compounds using ruthenium-based catalysts

Popis výsledku anglicky

Hydrogenation of dienes is an important chemical transformation in various fields such as organic synthesis, pharmacochemistry, and industrial chemistry. Selective hydrogenation of conjugated diene compounds is a challenging task. The hydrogenation may be brought about by either 1,2-addition or 1,4-addition. It is well known that the positions of the double bond and functional groups can significantly affect the properties of the product. For these reasons, it is crucial to find a suitable regio-and stereoselective catalytic complex to perform the hydrogenation step. It should be noted that the ratio of products of 1,2-and 1,4-addition, as well as the proportion of Z-and E-isomers, depends on the thermodynamic stability of intermediates and final compounds, the presence of substituents on C=C bonds, the configuration of C=C bonds and also on the properties of the catalyst. The presented review considers the main homogeneous and heterogeneous catalysts based on ruthenium that are used for the hydrogenation of dienes and compounds with a conjugated diene system. Hydrogenation in the presence of supported ruthenium catalysts (Ru/C, Ru/Al2O3) takes place with low selectivity, the 1,4-addition of hydrogen to double C=C bonds do not occur and products of 1,2-addition and saturated compounds are mainly formed. Homogeneous Ru-based catalysts are in most cases highly active and the major product is formed mainly by 1,4-addition. The stereoselectivity of the reaction is significantly dependent on the structure of the catalyst and the type of organic ligands present in the structure. The catalytic performance of ruthenium complexes containing phosphine ligands was studied in the regioselective hydrogenation of dienoic acids. Complexes catalyze the 1,4-addition with moderate regioand stereoselectivity. Ruthenium complexes containing the ligand 1,2,3,4,5-pentamethylcyclopentadienyl (Cp*) in the structure were also applied to perform the hydrogenation of diene compounds. It was found that the presence of the Cp* ligand in the complex structure has a positive effect on both the stability and activity of Ru complexes compared to other ligands. Ruthenium half-sandwich complexes [Cp*Ru (diene compound)]+ were used as catalysts for the hydrogenation of diene compounds. These reactions show high regioselectivity to 1,4-addition products and 100% stereoselectivity to products with Z-configuration of the double bond. © 2023 Nova Science Publishers, Inc.

Druh

C - Kapitola v odborné knize

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název knihy nebo sborníku

The Chemistry of Elements: Rubidium, Tellurium, Ruthenium and Gadolinium

ISBN

979-8-88697-965-7

Počet stran výsledku

33

Strana od-do

137-169

Počet stran knihy

258

Název nakladatele

Nova Science Publishers, Inc.

Místo vydání

New York

Kód UT WoS kapitoly

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