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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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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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Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.4K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.4K
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 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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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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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Aminación de areno C-H catalizado por dirodio utilizando hidroxilaminas

Mahesh P Paudyal1, Adeniyi Michael Adebesin1, Scott R Burt2

  • 1Division of Chemistry, Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, TX 75390, USA.

Science (New York, N.Y.)
|September 10, 2016
PubMed
Resumen

Este estudio introduce un nuevo método de aminación C-H catalizado por dirodio. Convierte eficientemente los compuestos aromáticos en arilaminas valiosas utilizando nuevos agentes aminantes.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • Las arylaminas son bloques de construcción cruciales en productos farmacéuticos, agroquímicos y ciencia de los materiales.
  • Los métodos existentes para la síntesis directa de arylamina a menudo carecen de generalidad o requieren condiciones duras.

Objetivo del estudio:

  • Desarrollar un método de aplicación amplia y suave para la aminación directa C-H de compuestos aromáticos.
  • Para sintetizar arylaminas primarias y N-alquilo a partir de diversos precursores aromáticos.

Principales métodos:

  • Utilizó un catalizador de dirodio para las reacciones de aminación C-H.
  • Utilizan NH2/NH ((alquilo)) -O ((sulfonilo)) hidroxilaminas como nuevos agentes aminantes con un oxidante interno.
  • Aplicó el método a varios sistemas aromáticos monocíclicos y fundidos.

Principales resultados:

  • Se logra la conversión directa de enlaces aromáticos C-H en enlaces C-N, formando arylaminas.
  • Se han demostrado rendimientos de moderados a buenos y una buena regioselectividad en condiciones suaves y escalables.
  • Extendió con éxito la metodología para sintetizar heterociclos N fusionados.

Conclusiones:

  • Presentado un versátil y eficiente protocolo de aminación C-H catalizado por dirodio.
  • El método desarrollado ofrece una vía práctica para diversas arylaminas y heterociclos N.
  • Este avance aborda la necesidad de estrategias sintéticas accesibles en química medicinal y de materiales.