Jove
Visualize
Contáctanos
JoVE
x logofacebook logolinkedin logoyoutube logo
ACERCA DE JoVE
Visión GeneralLiderazgoBlogCentro de Ayuda JoVE
AUTORES
Proceso de PublicaciónConsejo EditorialAlcance y PolíticasRevisión por ParesPreguntas FrecuentesEnviar
BIBLIOTECARIOS
TestimoniosSuscripcionesAccesoRecursosConsejo Asesor de BibliotecasPreguntas Frecuentes
INVESTIGACIÓN
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchivo
EDUCACIÓN
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualCentro de Recursos para ProfesoresSitio de Profesores
Términos y Condiciones de Uso
Política de Privacidad
Políticas

Videos de Conceptos Relacionados

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
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.
2.4K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.3K
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.
9.3K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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

3.3K
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.’
3.3K
Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

9.6K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
9.6K
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives

3.8K
Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of...
3.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.0K
  1. Home
  3. Acoplamiento Reductor Enantioselectivo Catalizado Por Cuh De Alquenos De Arilo Y Ácidos Carboxílicos Activados
  1. Home
  3. Acoplamiento Reductor Enantioselectivo Catalizado Por Cuh De Alquenos De Arilo Y Ácidos Carboxílicos Activados

Video Experimental Relacionado

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.5K

Acoplamiento reductor enantioselectivo catalizado por CuH de alquenos de arilo y ácidos carboxílicos activados

Jeffrey S Bandar1, Erhad Ascic1, Stephen L Buchwald1

  • 1Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society
|April 29, 2016

Ver abstracta en PubMed

Resumen
Este resumen es generado por máquina.

Un nuevo método catalizado por hidruro de cobre permite el acoplamiento reductor enantioselectivo de alquenos arílicos con derivados de ácido carboxílico. Este enfoque produce cetonas o alcoholes enantioenriquecidos con alta estereoselectividad y amplia tolerancia de grupo funcional.

Más Videos Relacionados

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

10.0K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K

Videos de Experimentos Relacionados

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.5K
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

10.0K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

8.0K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis estereoselectiva

Sus antecedentes:

  • El desarrollo de métodos eficientes para crear moléculas quirales es crucial en la química sintética.
  • Las reacciones de acoplamiento reductivo son valiosas para la formación de enlaces carbono-carbono.
  • La catálisis del cobre ofrece una plataforma versátil para diversas transformaciones orgánicas.

Objetivo del estudio:

  • Introducir un nuevo método de acoplamiento reductor enantioselectivo.
  • Para explorar los ciclos catalíticos duales que involucran el hidruro de cobre.
  • Para sintetizar cetonas y alcoholes enantioenriquecidos con α-sustitución.

Principales métodos:

  • Utilizando la catálisis del hidruro de cobre para el acoplamiento reductivo.
  • Utilizando como sustratos alquenos de arilo y derivados de ácido carboxílico activado.
  • Investigación de ciclos catalíticos duales: hidroacilación enantioselectiva seguida de reducción de cetonas diastereoselectiva.

    • Principales resultados:

    • Se ha logrado el acoplamiento reductor enantioselectivo de alquenos arilo.
    • Se han demostrado ciclos catalíticos duales con velocidades distintas.
    • Cetonas y alcoholes enantioenriquecidos sintetizados con una excelente estereoselectividad.
    • Se ha demostrado una amplia tolerancia del grupo funcional utilizando anhídridos arilo carboxílicos simétricos.

    Conclusiones:

    • El método desarrollado proporciona una ruta poderosa a las cetonas y alcoholes quirales.
    • Los ciclos catalíticos duales son clave para la estereoselectividad observada.
    • La catálisis del hidruro de cobre es eficaz para desafíos sintéticos complejos.