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Videos de Conceptos Relacionados

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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Introduction
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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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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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

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Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.       
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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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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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Endo-hidroamidación intramolecular selectiva habilitada por catálisis de NiH que incluye isomerización de

Hoonchul Choi1,2, Xiang Lyu1,2, Dongwook Kim1,2

  • 1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Daejeon 34141, South Korea.

Journal of the American Chemical Society
|May 27, 2022
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce una nueva reacción de hidroamidación intramolecular catalizada por hidróxido de níquel. El método logra una excelente endo-selectividad para la síntesis de valiosas enamidas cíclicas, incluidos los anillos azacíclicos más grandes.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La hidroamidación intramolecular de alquina es clave para la síntesis de la enamida cíclica.
  • El logro de un control de región preciso, especialmente la endociclización para anillos más grandes, sigue siendo un desafío.

Objetivo del estudio:

  • Desarrollar un método catalizado por NiH para la hidroamidación intramolecular altamente endoselectiva.
  • Para sintetizar enamidas endocíclicas de seis a ocho miembros con un amplio alcance.

Principales métodos:

  • Hidroamidación intramolecular catalizada por hidróxido de níquel (NiH) de las dioxazolonas de alquinyl.
  • Estudios mecanicistas que incluyen la catálisis del Ni (I), la sinhidronicelación y la isomerización del alquenil níquel.

Principales resultados:

  • Se obtiene una excelente endo-selectividad en la reacción de hidroamidación.
  • Sintetizó una variedad de enamidas endocíclicas de seis a ocho miembros.
  • Elucidado el mecanismo, incluida una isomerización clave de alquenilníquel a través de un estado de transición de vinilo eta-2.

Conclusiones:

  • El protocolo catalizado por NiH desarrollado proporciona una ruta robusta a las enamidas endocíclicas.
  • Las ideas mecanicistas, particularmente el paso de isomerización, avanzan en la comprensión de las reacciones de hidroamidación.
  • Las enamidas sintetizadas sirven como precursores valiosos para andamios delta-lactámicos altamente funcionales.