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

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

1.7K
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.
1.7K
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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

2.9K
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.’
2.9K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.9K
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.
1.9K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.0K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.0K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

3.4K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
3.4K

También podría leer

Artículos Relacionados

Artículos vinculados a este trabajo por autores compartidos, revista y gráfico de citas.

Ordenar por
Same author

Radical Coupling Initiated by Organophosphine Addition to Ynoates.

Angewandte Chemie (International ed. in English)·2023
Same author

Intramolecular photochemical [2 + 1]-cycloadditions of nucleophilic siloxy carbenes.

Chemical science·2022
Same author

Bioinspired Total Synthesis of Erectones A and B, and the Revised Structure of Hyperelodione D.

Angewandte Chemie (International ed. in English)·2022
Same author

Flow-Assisted Synthesis of Alkyl Citrate Natural Products.

The Journal of organic chemistry·2021
Same author

Photoexcited Pd(ii) auxiliaries enable light-induced control in C(sp<sup>3</sup>)-H bond functionalisation.

Chemical science·2021
Same author

Fluorinated Ketones as Trapping Reagents for Visible-Light-Induced Singlet Nucleophilic Carbenes.

Organic letters·2021
Same journal

On-Cell Detection of Polysaccharide One-Bond <sup>1</sup>J<sub>CH</sub> Couplings by Proton-Detected Solid-State NMR.

Journal of the American Chemical Society·2026
Same journal

Correction to "Unraveling the Effects of Fe Incorporation on High-Performance Water-Splitting Photoanodes".

Journal of the American Chemical Society·2026
Same journal

Proximity-Driven Protein Ligation Beyond the Concentration Limit.

Journal of the American Chemical Society·2026
Same journal

GraPhAI: Neural Networks for Solving Centrosymmetric Crystal Structures.

Journal of the American Chemical Society·2026
Same journal

Probing Stage Transition Kinetics in Li-Graphite Intercalation Compounds by Time-Resolved In Situ Solid-State NMR via <sup>13</sup>C Labeling.

Journal of the American Chemical Society·2026
Same journal

Dynamic Covalent Programming at DNA Base-Pairing Interfaces.

Journal of the American Chemical Society·2026
Ver todos los artículos relacionados

Video Experimental Relacionado

Updated: Jun 10, 2025

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

7.4K

Acoplamiento reductivo y desodorizante de alqueno-aldehído inducido por electrones

Liam J Franov1, Tayla L Wilsdon1, Milena L Czyz1

  • 1School of Chemistry, The University of Melbourne, Parkville, Victoria 3010, Australia.

Journal of the American Chemical Society
|October 17, 2024
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un nuevo método electroquímico para acoplar alquenos y heteroarenos con aldehídos, creando diversos alcoholes híbridos C ((sp3). Este enfoque libre de catalizadores supera las limitaciones de los métodos actuales para sintetizar andamios complejos oxigenados.

Más Videos Relacionados

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

13.0K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

9.9K

Videos de Experimentos Relacionados

Last Updated: Jun 10, 2025

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

7.4K
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

13.0K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

9.9K

Área de la Ciencia:

  • Química orgánica
  • La electroquímica
  • Metodología sintética

Sus antecedentes:

  • El acoplamiento directo de alquenos y aldehídos es difícil debido a las limitaciones en la tolerancia del sustrato y la compatibilidad del grupo funcional.
  • Los métodos existentes para el acoplamiento de enlaces C-C π con aldehídos a menudo están restringidos en entornos moleculares complejos.

Objetivo del estudio:

  • Desarrollar un método eficiente y versátil para el acoplamiento directo de alquenos simples, heteroarenos y aldehídos alifáticos no activados.
  • Para permitir la síntesis de diversos alcoholes híbridos de C ((sp3) a partir de materias primas fácilmente disponibles.

Principales métodos:

  • Se utilizó la activación reductora inducida electroquímicamente de los enlaces C-C π mediante electrólisis de polaridad alterna rápida (rAP).
  • Condiciones libres de catalizadores empleadas para el proceso de acoplamiento reductivo.
  • Investigó la generación y la reactividad de los intermediarios de aniones radicales.

Principales resultados:

  • Se logra el acoplamiento directo de alquenos y heteroarenos con aldehídos alifáticos, obteniendo diversos alcoholes híbridos C ((sp3).
  • Se ha demostrado la generación quimioselectiva de intermediarios de aniones de radicales olefínicos mediante la electrólisis de rAP.
  • Funcionalización reductora y aromática sin precedentes para los compuestos heterocíclicos.

Conclusiones:

  • El protocolo de electrólisis rAP desarrollado proporciona una vía versátil y eficiente para los andamios oxigenados ricos en C ((sp3).
  • Este método sin catalizador amplía el alcance de las reacciones de acoplamiento reductivo para la síntesis orgánica.
  • Ofrece un acceso directo a productos alcohólicos estructuralmente diversos a partir de materias primas simples.