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

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

4.9K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
4.9K
Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

4.3K
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
4.3K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

7.6K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
7.6K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.1K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
13.1K
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

2.3K
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.
2.3K
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

También podría leer

Artículos Relacionados

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

Ordenar por
Same author

Installing Axial Chirality by Atroposelective C(sp<sup>3</sup>)-H Bond Oxidation.

Journal of the American Chemical Society·2026
Same author

Regioselective Oxidative Coupling of Monohalogenated Phenols.

Organic letters·2026
Same author

Ortho-Ortho Selective Oxidative Coupling of Phenols by Hydroxo Multicopper(II) Clusters.

Journal of the American Chemical Society·2025
Same author

Halogen Bond-Driven Ligand Displacement: Co-Crystal Lattice Versus Coordination Bonds.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Chiral Bis-8-Aryl-isoquinoline Bis-alkylamine Iron Catalysts for Asymmetric Oxidation Reactions.

Organic letters·2025
Same author

Dynamic Thermodynamic Resolution of Racemic 1,1'-Binaphthyl-2,2'-diol (BINOL).

Organic letters·2024

Video Experimental Relacionado

Updated: Feb 23, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K

Cloruro de hierro de meso-tetrafenilporfirina catalizado por acoplamiento cruzado selectivo oxidativo de fenoles

Hadas Shalit1, Anna Libman1, Doron Pappo1

  • 1Department of Chemistry, Ben-Gurion University of the Negev , Beer-Sheva 84105, Israel.

Journal of the American Chemical Society
|September 2, 2017
PubMed
Resumen

Un nuevo catalizador de hierro permite un acoplamiento oxidativo eficiente de fenoles, creando bifenolos asimétricos a partir de socios menos reactivos. Este método escalable amplía el acceso a estructuras químicas valiosas.

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

13.6K
[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

9.9K

Videos de Experimentos Relacionados

Last Updated: Feb 23, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.9K
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

13.6K
[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

9.9K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Ciencias de los materiales

Sus antecedentes:

  • Las reacciones de acoplamiento cruzado oxidativo son cruciales para sintetizar moléculas orgánicas complejas.
  • El desarrollo de catalizadores selectivos para acoplar socios fenólicos menos reactivos sigue siendo un desafío.

Objetivo del estudio:

  • Desarrollar un nuevo sistema catalítico para el acoplamiento cruzado oxidativo de fenoles fácilmente oxidados con socios fenólicos poco nucleófilos.
  • Investigar el mecanismo y la escalabilidad del sistema catalítico desarrollado.

Principales métodos:

  • Utilizó un complejo de cloruro de ferro meso-tetrafenilporfirina (Fe[TPP]Cl) como catalizador.
  • Se utiliza el 1,1,1,3,3-hexafluoropropan-2-ol (HFIP) como solvente de la reacción.
  • Caracterizó los productos de reacción y exploró el mecanismo que involucra a los radicales fenoxilo y los intermedios ligados al hierro.

Principales resultados:

  • Se ha logrado un acoplamiento oxidativo eficiente de varios fenoles, incluidos los que contienen sustituyentes de alquilo o haluro.
  • Se ha demostrado una quimioselectividad única atribuida a la interacción entre los radicales fenoxilo y los socios fenólicos ligados al hierro.
  • Escaló con éxito las condiciones de reacción para la preparación de una amplia gama de bifenolos asimétricos.

Conclusiones:

  • El sistema Fe[TPP]Cl/HFIP desarrollado proporciona un método escalable y selectivo para sintetizar bifenolos asimétricos.
  • Este sistema catalítico supera las limitaciones asociadas con los socios fenólicos nucleófilos pobres.
  • Los resultados ofrecen una herramienta valiosa para la síntesis orgánica y las aplicaciones de la ciencia de los materiales.