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Videos de Conceptos Relacionados

Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
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Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Preparation of Nitriles01:12

Preparation of Nitriles

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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Introducción de la aminación catalítica de los silanos mediante la inserción de nitreno

Anabel M Rodríguez1, Jorge Pérez-Ruíz1, Francisco Molina1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain.

Journal of the American Chemical Society
|June 1, 2022
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Resumen

Este estudio introduce un nuevo método para la funcionalización directa de enlaces silicio-hidrógeno (Si-H) mediante la inserción de nitreno. Un catalizador de cobre facilita la formación eficiente de enlaces silicio-nitrógeno (Si-NH) en varios compuestos que contienen silicio.

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Área de la Ciencia:

  • Química organometálica
  • Química del silicio
  • Catálisis

Sus antecedentes:

  • La funcionalización directa de los enlaces silicio-hidrógeno (Si-H) sigue siendo un desafío importante en la química del organosilicio.
  • Las reacciones de inserción de nitreno son herramientas poderosas para la formación de enlaces C-N, pero su aplicación a los enlaces Si-H es menos explorada.

Objetivo del estudio:

  • Desarrollar un nuevo método catalítico para la funcionalización directa de los enlaces Si-H mediante la inserción de nitreno.
  • Investigar el alcance y las limitaciones de esta nueva transformación.
  • Para aclarar el mecanismo de reacción subyacente.

Principales métodos:

  • Se utilizó un complejo de cobre con un ligando de trispirazolilborato.
  • Utilizó PHINOS como fuente de nitrógeno.
  • Probó la reacción con varios silanos, disilanos y siloxanos.
  • Ha realizado cálculos basados en la teoría de la densidad funcional (DFT) para estudios mecanicistas.

Principales resultados:

  • Se obtiene la formación exclusiva de fracciones de Si-NH mediante la inserción de nitreno en enlaces de Si-H.
  • Se ha demostrado la actividad catalítica del complejo de cobre.
  • Muestra tolerancia hacia otros grupos funcionales como los enlaces C-H, alquino y alqueno unidos al silicio.
  • Los cálculos de DFT apoyaron un mecanismo que involucra la escisión homolítica de Si-H y el rebote radical.

Conclusiones:

  • Estableció un nuevo y eficiente método para la funcionalización de enlaces Si-H utilizando la catálisis de inserción de nitrógeno.
  • La metodología desarrollada ofrece una vía versátil para los compuestos de Si-NH con un amplio alcance de sustrato.
  • Los conocimientos mecanicistas proporcionan una base para un mayor desarrollo en la catálisis basada en silicio.