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Videos de Conceptos Relacionados

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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Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

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Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

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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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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

13.1K
Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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9.2K
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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Eterificación reductiva mediante catálisis por unión de aniones

Chenfei Zhao1, Christopher A Sojdak1, Wazo Myint1

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.

Journal of the American Chemical Society
|July 26, 2017
PubMed
Resumen
Este resumen es generado por máquina.

Un nuevo organocatalisador de tiureo permite la síntesis de éteres reductores a partir de alcoholes y aldehídos/cetonas utilizando un simple agente reductor de siloxano. Este método ofrece un amplio alcance de sustrato y tolerancia de grupo funcional, suprimiendo las reacciones secundarias no deseadas para una producción eficiente de éter.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La síntesis del éter es crucial en la química orgánica.
  • Los métodos existentes a menudo requieren condiciones duras o reactivos especializados.
  • Es necesario desarrollar sistemas catalíticos eficientes y selectivos.

Objetivo del estudio:

  • Desarrollar un nuevo método organocatalítico para la síntesis de éter reductor.
  • Utilizar catalizadores y reactivos fácilmente accesibles.
  • Para lograr una alta eficiencia y selectividad para sustratos difíciles.

Principales métodos:

  • Condensación reductora de los alcoholes con aldehídos o cetonas.
  • Catalización con un organocatalizador de tiureo y ácido clorhídrico (HCl).
  • Utilizando 1,1,3,3-tetrametildisiloxano como agente reductor.

Principales resultados:

  • Síntesis exitosa de éteres a través de la condensación reductora.
  • Aplicabilidad demostrada a combinaciones de sustratos difíciles.
  • Exhibió una excelente tolerancia al grupo funcional.
  • Se ha suprimido el homoacoplamiento reductor de compuestos carbonílicos.

Conclusiones:

  • Se ha establecido un sistema organocatalítico práctico y eficiente para la síntesis de éter.
  • El método ofrece una valiosa alternativa a las rutas sintéticas existentes.
  • El catalizador y las condiciones son robustos y versátiles para diversas aplicaciones.