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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

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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

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Creación y estabilización de una superficie Pd oxidada bajo condiciones reductivas para la hidrogenación

Wei Qiao1,2, Xing Fan3, Weifeng Liu4

  • 1Soochow Institute for Energy and Materials Innovations (SIEMIS), Soochow University, Suzhou 215006, China.

Journal of the American Chemical Society
|February 28, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo método fotocatalítico para la conversión de carbonilos aromáticos en aromáticos libres de O. Un cocatalizador de óxido de paladio (PdO) en nitruro de carbono grafítico permite una acetalización e hidrogenación eficientes en condiciones suaves.

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Área de la Ciencia:

  • Catálisis
  • Ciencias de los materiales
  • Química ecológica

Sus antecedentes:

  • La fotocatálisis ofrece una alternativa ecológica para la hidrogenación de carbonilo aromático.
  • Los métodos convencionales requieren alta presión y temperatura, y a menudo resultan en una desoxigenación incompleta.
  • Los carbonilos aromáticos son sustratos difíciles para la desoxigenación completa en condiciones ambientales.

Objetivo del estudio:

  • Desarrollar una vía fotocatalítica eficiente y selectiva para la producción de aromáticos libres de O a partir de carbonilos aromáticos.
  • Investigar una nueva vía de hidrogenación que implique la acetalización y la posterior hidrogenación.
  • Mejorar el rendimiento y la estabilidad de los fotocatalizadores para esta transformación.

Principales métodos:

  • Construcción de un cocatalizador de óxido de paladio (PdO) apoyado en nitruro de carbono grafítico.
  • Hidrogenación fotocatalítica de carbonilos aromáticos mediante irradiación con luz visible (410 nm).
  • Optimización de las condiciones de reacción, incluida la adición de trazas de HCl para la estabilidad.

Principales resultados:

  • La superficie de PdO facilitó una vía de acetalización e hidrogenación gradual, lo que condujo a una desoxigenación eficiente.
  • La hidrogenación fotocatalítica del benzaldehído al tolueno alcanza una selectividad > 90%.
  • Se observó una eficiencia cuántica de aproximadamente el 10,2%.
  • El catalizador demostró estabilidad y actividad a largo plazo en presencia de trazas de HCl.

Conclusiones:

  • El sistema PdO/nitruro de carbono grafítico desarrollado proporciona una estrategia eficaz para la síntesis selectiva de aromáticos libres de O mediante fotocatálisis.
  • La química de la superficie única de PdO promueve la vía deseada de acetalización-hidrogenación.
  • Este enfoque ofrece una alternativa prometedora y sostenible a los procesos tradicionales de refinación para la producción de aromáticos libres de O.