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

Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

3.8K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
3.8K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
Free-Radical Chain Reaction and Polymerization of Alkenes02:35

Free-Radical Chain Reaction and Polymerization of Alkenes

7.8K
The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
7.8K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K

También podría leer

Artículos Relacionados

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

Ordenar por
Same author

A Unified Platform for Direct Alkynylation from Alcohols via Deoxygenative Metallaphotoredox Catalysis.

Journal of the American Chemical Society·2026
Same author

High-Precision Intrinsic Interactome Elucidation of Chimeric Antigen Receptors via Photocatalytic Micromapping (μMap-CAR).

Journal of the American Chemical Society·2026
Same author

Piecewise Stereoselective Assembly of Multisubstituted Alkenes.

Journal of the American Chemical Society·2026
Same author

Oxyalkylation of Alkenes via Triple Radical Sorting.

Journal of the American Chemical Society·2026
Same author

Deaminative C(<i>sp</i><sup>3</sup>)─C(<i>sp</i><sup>3</sup>) Cross-Coupling of Benzylamines with Alcohols and Carboxylic Acids via Radical Sorting.

Journal of the American Chemical Society·2026
Same author

Deoxycyanation of Alkyl Alcohols Using Photoredox Catalysis.

Organic letters·2026

Video Experimental Relacionado

Updated: Jul 3, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

10.8K

Dialquilación de alquenos por clasificación de radicales triples

Johnny Z Wang1, William L Lyon1, David W C MacMillan2

  • 1Merck Center for Catalysis at Princeton University, Princeton, NJ, USA.

Nature
|February 13, 2024
PubMed
Resumen

La catálisis de sustitución homolítica bimolécula (SH2) permite la clasificación selectiva de radicales para la formación de enlaces C{\displaystyle C} -C{\displaystyle C} . Este nuevo método logra la dialquilación de alceno mediante la diferenciación de tres especies radicales, acelerando la síntesis de moléculas complejas.

Más Videos Relacionados

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
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.3K

Videos de Experimentos Relacionados

Last Updated: Jul 3, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

10.8K
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
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.3K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La catálisis de sustitución homolítica bimolécula (SH2) ha avanzado en las reacciones de acoplamiento cruzado.
  • Los métodos SH2 existentes permiten la combinación selectiva de radicales primarios, secundarios o terciarios.
  • Un desafío clave sigue siendo la dialquilación simultánea de alquenos a través de la clasificación radical.

Objetivo del estudio:

  • Desarrollar un nuevo enfoque catalítico SH2 para la dialquilación de alquenos.
  • Para permitir la construcción simultánea de dos enlaces C{\displaystyle C} -C{\displaystyle C}
  • Para superar las limitaciones de la recombinación estadística de radicales y las reacciones secundarias.

Principales métodos:

  • Utilizando la catálisis de sustitución homolítica bimolecular (SH2).
  • Generación in situ de tres especies radicales distintas.
  • Empleando una clasificación radical basada en el tamaño y las propiedades electrónicas.

Principales resultados:

  • Se ha logrado la dialquilación regioselectiva de alquenos no activados.
  • Se clasificaron con éxito los radicales electrófilos y nucleófilos a través de alquenos.
  • Demostró una nueva vía para la formación de enlaces C-C.

Conclusiones:

  • Este trabajo establece un enfoque mecanicista distinto para la dialquilación de alquenos.
  • La catálisis SH2 desarrollada acelera el acceso a moléculas ricas en C3.
  • Esta metodología amplía el alcance de las reacciones de acoplamiento cruzado basadas en radicales.