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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
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Introduction
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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Catalizador de electridos intermetálicos a base de cobre para las reacciones de hidrogenación quimioselectiva

Tian-Nan Ye^1,2, Yangfan Lu^1,2, Jiang Li^1,2

¹Materials Research Center for Element Strategy, Tokyo Institute of Technology , 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, Japan.

Journal of the American Chemical Society

|November 4, 2017

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Un nuevo catalizador de electruro intermetálico basado en cobre, LaCu_0.67Si_1.33, mejora significativamente la hidrogenación del nitroareno. Este catalizador exhibe una actividad y estabilidad superiores en comparación con los catalizadores metálicos tradicionales debido a sus propiedades electrónicas únicas.

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Área de la Ciencia:

Ciencias de los materiales
Catálisis
Química de las superficies

Sus antecedentes:

Los compuestos intermetálicos de metales de transición ofrecen estructuras sintonizables para una catálisis mejorada.
La incorporación de sitios activos dentro de los marcos de celosía modula las propiedades electrónicas y el rendimiento catalítico.

Objetivo del estudio:

Desarrollar un nuevo catalizador de electridos intermetálicos a base de cobre para la hidrogenación selectiva.
Investigar la actividad catalítica, la selectividad y la estabilidad del nuevo material.

Principales métodos:

Síntesis y caracterización del electrido intermetálico LaCu_0.67Si_1.33.
Evaluación del rendimiento catalítico en la hidrogenación del nitroareno.
Análisis cinético utilizando efectos isotópicos para determinar el paso determinante de la velocidad.

Principales resultados:

LaCu_0.67Si_1.33 demuestra más de 40 veces más altas frecuencias de rotación (hasta 5084 h^-1) para la hidrogenación de nitroareno en comparación con los catalizadores cargados de metal.
El catalizador exhibe una baja energía de activación (14,8 kJ·mol^-1) para la activación de hidrógeno debido a la alta densidad del portador y la baja función de trabajo.
La alta quimioselectividad se logra a través de la adsorción preferencial de nitroarenos a través del grupo nitro, facilitada por la afinidad del catalizador con el oxígeno.

Conclusiones:

El catalizador de electruro LaCu_0.67Si_1.33 supera a los catalizadores convencionales cargados de metal en actividad y estabilidad para la hidrogenación de nitroareno.
El marco de celosía único y las propiedades electrónicas del compuesto intermetálico son cruciales para su función catalítica mejorada.
Este trabajo pone de relieve el potencial de los metales de transición integrados en sitios de celosía específicos como centros catalíticos altamente eficientes.