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Videos de Conceptos Relacionados

Reduction of Alkenes: Catalytic Hydrogenation02:13

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.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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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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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

7.7K
The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Hidrogenación electrocatalítica de los alquenos y desuteración

Faxiang Bu1, Yuqi Deng1, Lijun Lu1

  • 1College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS), Wuhan University, Wuhan 430072, P. R. China.

Journal of the American Chemical Society
|February 4, 2025
PubMed
Resumen

Este estudio presenta un método electrocatalítico universal para la reducción de alquenos utilizando agua como fuente de hidrógeno, evitando el peligroso gas de hidrógeno a alta presión. Este enfoque de química verde ofrece altos rendimientos para varios alquenos y moléculas complejas.

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Área de la Ciencia:

  • Química orgánica
  • Química ecológica
  • La electroquímica

Sus antecedentes:

  • Los métodos tradicionales de reducción de alquenos, como los reductores estequiométricos y la hidrogenación catalítica, plantean preocupaciones ambientales y de seguridad debido a la generación de residuos y al gas de hidrógeno a alta presión.
  • Se necesitan alternativas sostenibles y más seguras para la reducción de alceno en la síntesis orgánica.

Objetivo del estudio:

  • Desarrollar un método universal y respetuoso con el medio ambiente para la hidrogenación electrocatalítica y la deuteración de alquenos.
  • Utilizar agua (H2O) y agua pesada (D2O) como fuentes sostenibles de hidrógeno y deuterio, respectivamente, en condiciones ambientales.

Principales métodos:

  • Reducción electrocatalítica de alquenos mediante el uso de electrodos modificados.
  • Generación de especies activas de hidruro metálico (M-H) y deuteruro metálico (M-D) por electrólisis de H2O/D2O en electrodos modificados.
  • Condiciones de temperatura y presión ambiente, evitando la necesidad de gas H2 o D2.

Principales resultados:

  • Reducción y deuteración exitosas de una amplia gama de alquenos, incluidos los mono-, di-, tri- y tetrasubstituidos, donantes/retiradores de electrones, y aquellos con otros grupos funcionales reducibles.
  • Se obtuvieron altos rendimientos (hasta el 99%) para 85 ejemplos, incluidos productos naturales complejos y medicamentos.
  • Excelente eficiencia de Faraday que alcanza el 84% y una disminución significativa de la carga metálica catalítica a menos del 0,01 mol%.

Conclusiones:

  • El método electrocatalítico desarrollado proporciona un enfoque seguro, eficiente y versátil para la hidrogenación y deuteración de alquenos.
  • Este método ofrece una alternativa sostenible a las técnicas tradicionales de reducción, minimizando los residuos y los riesgos para la seguridad.
  • La baja carga del catalizador y la alta eficiencia hacen de esta una técnica prometedora tanto para la investigación académica como para aplicaciones industriales.