A new non-cinchona chiral modifier immobilized on Pt/SiO2 catalysts for enantioselective heterogeneous hydrogenation

Cristian H. Campos, Cecilia C. Torres, Ariel Leyton, Julio Belmar, Claudio Mella, Paula Osorio-Vargas, Doris Ruiz, José L.G. Fierro, Patricio Reyes

Resultado de la investigación: Article

4 Citas (Scopus)

Resumen

Pt heterogeneous catalysts were prepared by the covalent immobilization of (4′R,5′S)-4′,5′-dihydro-4′,5′-diphenyl-2-(6-cyanopyridyl)imidazoline (PyIm) as the asymmetric modifier. These novel series of catalysts were studied in the 1-phenyl-1,2-propanodione (PPD) hydrogenation. The effects of the PyIm surface concentration, hydrogen pressure, solvent nature and recycles on the reaction were studied. These modified catalysts represent the first effective immobilized chiral non-Cinchona-type modifier of Pt for the enantioselective hydrogenation. The enantio-differentiation was attributed to the substrate-modifier interactions involving hydrogen bonding between the keto-carbonyl O atom and the NH moiety PyIm. The results confirmed that the variations in the H2 pressure and the solvent affect the activity and the enantioselectivity due to the substrate adsorption on the active sites of the metal. Additionally, this heterogeneous catalyst can be conveniently reused at least five times without loss of its catalytic efficiency, but the enantioselectivity decreased, which may be due to the leaching of the modifier.

Idioma originalEnglish
Páginas (desde-hasta)76-87
Número de páginas12
PublicaciónApplied Catalysis A: General
Volumen498
DOI
EstadoPublished - 5 jun 2015

Huella dactilar

Hydrogenation
Catalysts
Enantioselectivity
Imidazolines
Substrates
Leaching
Hydrogen
Hydrogen bonds
Metals
Adsorption
Atoms

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology

Citar esto

Campos, Cristian H. ; Torres, Cecilia C. ; Leyton, Ariel ; Belmar, Julio ; Mella, Claudio ; Osorio-Vargas, Paula ; Ruiz, Doris ; Fierro, José L.G. ; Reyes, Patricio. / A new non-cinchona chiral modifier immobilized on Pt/SiO2 catalysts for enantioselective heterogeneous hydrogenation. En: Applied Catalysis A: General. 2015 ; Vol. 498. pp. 76-87.
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abstract = "Pt heterogeneous catalysts were prepared by the covalent immobilization of (4′R,5′S)-4′,5′-dihydro-4′,5′-diphenyl-2-(6-cyanopyridyl)imidazoline (PyIm) as the asymmetric modifier. These novel series of catalysts were studied in the 1-phenyl-1,2-propanodione (PPD) hydrogenation. The effects of the PyIm surface concentration, hydrogen pressure, solvent nature and recycles on the reaction were studied. These modified catalysts represent the first effective immobilized chiral non-Cinchona-type modifier of Pt for the enantioselective hydrogenation. The enantio-differentiation was attributed to the substrate-modifier interactions involving hydrogen bonding between the keto-carbonyl O atom and the NH moiety PyIm. The results confirmed that the variations in the H2 pressure and the solvent affect the activity and the enantioselectivity due to the substrate adsorption on the active sites of the metal. Additionally, this heterogeneous catalyst can be conveniently reused at least five times without loss of its catalytic efficiency, but the enantioselectivity decreased, which may be due to the leaching of the modifier.",
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A new non-cinchona chiral modifier immobilized on Pt/SiO2 catalysts for enantioselective heterogeneous hydrogenation. / Campos, Cristian H.; Torres, Cecilia C.; Leyton, Ariel; Belmar, Julio; Mella, Claudio; Osorio-Vargas, Paula; Ruiz, Doris; Fierro, José L.G.; Reyes, Patricio.

En: Applied Catalysis A: General, Vol. 498, 05.06.2015, p. 76-87.

Resultado de la investigación: Article

TY - JOUR

T1 - A new non-cinchona chiral modifier immobilized on Pt/SiO2 catalysts for enantioselective heterogeneous hydrogenation

AU - Campos, Cristian H.

AU - Torres, Cecilia C.

AU - Leyton, Ariel

AU - Belmar, Julio

AU - Mella, Claudio

AU - Osorio-Vargas, Paula

AU - Ruiz, Doris

AU - Fierro, José L.G.

AU - Reyes, Patricio

PY - 2015/6/5

Y1 - 2015/6/5

N2 - Pt heterogeneous catalysts were prepared by the covalent immobilization of (4′R,5′S)-4′,5′-dihydro-4′,5′-diphenyl-2-(6-cyanopyridyl)imidazoline (PyIm) as the asymmetric modifier. These novel series of catalysts were studied in the 1-phenyl-1,2-propanodione (PPD) hydrogenation. The effects of the PyIm surface concentration, hydrogen pressure, solvent nature and recycles on the reaction were studied. These modified catalysts represent the first effective immobilized chiral non-Cinchona-type modifier of Pt for the enantioselective hydrogenation. The enantio-differentiation was attributed to the substrate-modifier interactions involving hydrogen bonding between the keto-carbonyl O atom and the NH moiety PyIm. The results confirmed that the variations in the H2 pressure and the solvent affect the activity and the enantioselectivity due to the substrate adsorption on the active sites of the metal. Additionally, this heterogeneous catalyst can be conveniently reused at least five times without loss of its catalytic efficiency, but the enantioselectivity decreased, which may be due to the leaching of the modifier.

AB - Pt heterogeneous catalysts were prepared by the covalent immobilization of (4′R,5′S)-4′,5′-dihydro-4′,5′-diphenyl-2-(6-cyanopyridyl)imidazoline (PyIm) as the asymmetric modifier. These novel series of catalysts were studied in the 1-phenyl-1,2-propanodione (PPD) hydrogenation. The effects of the PyIm surface concentration, hydrogen pressure, solvent nature and recycles on the reaction were studied. These modified catalysts represent the first effective immobilized chiral non-Cinchona-type modifier of Pt for the enantioselective hydrogenation. The enantio-differentiation was attributed to the substrate-modifier interactions involving hydrogen bonding between the keto-carbonyl O atom and the NH moiety PyIm. The results confirmed that the variations in the H2 pressure and the solvent affect the activity and the enantioselectivity due to the substrate adsorption on the active sites of the metal. Additionally, this heterogeneous catalyst can be conveniently reused at least five times without loss of its catalytic efficiency, but the enantioselectivity decreased, which may be due to the leaching of the modifier.

KW - Chiral Pt catalysts

KW - Covalent immobilization

KW - Enantioselective hydrogenation

KW - Non-chincona modifiers

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U2 - 10.1016/j.apcata.2015.01.048

DO - 10.1016/j.apcata.2015.01.048

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EP - 87

JO - Applied Catalysis A: General

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SN - 0926-860X

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