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Videos de Conceptos Relacionados

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Electrophiles02:28

Electrophiles

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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

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Oxidation–Reduction Reactions
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Radical Reactivity: Electrophilic Radicals01:02

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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Acoplamiento reductivo entre electrófilos C-N y C-O

Rong-De He1, Chun-Ling Li1, Qiu-Quan Pan1

  • 1State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering , Lanzhou University , 222 South Tianshui Road , Lanzhou 730000 , China.

Journal of the American Chemical Society
|August 1, 2019
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce una nueva reacción de acoplamiento electrofilo cruzado, formando enlaces carbono-carbono mediante la escisión de enlaces carbono-nitrógeno y carbono-oxígeno. Esto expande las estrategias de formación de enlaces C-C más allá de los haluros orgánicos tradicionales.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética

Sus antecedentes:

  • Las reacciones electrofílicas cruzadas son clave para la formación de enlaces C-C.
  • Las investigaciones existentes utilizan principalmente haluros orgánicos como electrófilos.

Objetivo del estudio:

  • Para explorar la formación de enlaces C-C utilizando electrófilos C-N y C-O.
  • Para demostrar la escisión de los enlaces C-N y C-O en las reacciones de acoplamiento.

Principales métodos:

  • Reacciones de acoplamiento investigadas entre sales de bencilo/arilo amonio (electrófilos CN) y electrófilos vinilo/arilo CO.
  • Se han realizado estudios mecanicistas preliminares.

Principales resultados:

  • Se ha logrado con éxito la formación de enlaces C-C mediante la escisión de enlaces C-N y C-O.
  • Se identificó un mecanismo radical para la activación de bencilo amonio.

Conclusiones:

  • El estudio amplía el alcance de las reacciones electrofílicas cruzadas.
  • Los electrófilos C-N y C-O pueden usarse efectivamente para la construcción de enlaces C-C.