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 Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.3K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.3K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.6K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.1K
Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

6.1K
Overview
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
6.1K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.2K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.2K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.0K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.0K

También podría leer

Artículos Relacionados

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

Ordenar por
Same author

Photoinduced Copper-Catalyzed Site- and Stereoselective Desymmetrizing β-C(sp<sup>3</sup>)-H Alkynylation of Cycloalkyl Amines.

Journal of the American Chemical Society·2026
Same author

Osteoimmuno-brain axis: a bridge connecting osteoporosis and cognitive decline and its clinical significance in dementia and Alzheimer's disease.

Frontiers in immunology·2026
Same author

Zingerone alleviates diabetic nephropathy by interrupting the ER stress-inflammation-apoptosis cascade in streptozotocin-induced diabetic mice.

Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas·2026
Same author

Enlarged choroid plexus in chronic insomnia patients and its association with DTI-ALPS index alterations and cognitive decline.

Neuroradiology·2026
Same author

Nonprecious Metal-Modified Porous Organic Polymers for Enhanced Photocatalytic Degradation.

Langmuir : the ACS journal of surfaces and colloids·2026
Same author

Transition Metal-Free Borata-Alkene/Alkyne Metathesis Enables Access to Cyclopentenes.

Angewandte Chemie (International ed. in English)·2026

Video Experimental Relacionado

Updated: Sep 1, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K

Sustitución catalítica asimétrica vinílica y bisvinílica por propargilo

Hao-Dong Qian1, Zhi-Heng Li1, Shuang Deng2

  • 1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P.R. China.

Journal of the American Chemical Society
|August 17, 2022
PubMed
Resumen

Un nuevo ligando quiral N,N,P permite un control preciso de las reacciones catalizadas por cobre, produciendo compuestos carbonílicos no saturados alquínicos altamente enriquecidos con una amplia tolerancia de grupo funcional.

Más Videos Relacionados

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
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

13.1K

Videos de Experimentos Relacionados

Last Updated: Sep 1, 2025

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

7.0K
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

13.1K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Síntesis asimétrica

Sus antecedentes:

  • Las reacciones catalizadas por el cobre son cruciales en la síntesis orgánica.
  • El logro de una elevada regioselectividad y enantioselectividad en la sustitución de propargilo sigue siendo un reto.
  • El desarrollo de nuevos ligandos quirales es clave para avanzar en la catálisis asimétrica.

Objetivo del estudio:

  • Desarrollar un nuevo ligando quiral para la sustitución propargílica viníloga y bisviníloga catalizada por cobre.
  • Para lograr una distinta regionalidad y enantioselectividad en estas transformaciones.
  • Para sintetizar compuestos carbonílicos insaturados alquinílicos altamente enriquecidos con enantio.

Principales métodos:

  • Utilizó un nuevo ligando quiral N,N,P en reacciones catalizadas por cobre.
  • Se han investigado las reacciones de sustitución propargílica viníloga y bisviníloga.
  • Empleado una amplia gama de sustratos y grupos funcionales.

Principales resultados:

  • Se ha logrado un control distinto de la regionalidad y la enantiselectividad.
  • Desarrolló un método eficiente y selectivo para sintetizar compuestos objetivo.
  • Se ha demostrado una excelente tolerancia al grupo funcional y un amplio alcance en el sustrato.
  • Realizó con éxito la síntesis a escala de gramos y aplicó el método a transformaciones desafiantes.

Conclusiones:

  • El nuevo ligando quiral N,N,P es eficaz para controlar la selectividad en la sustitución propargílica catalizada por cobre.
  • El método desarrollado ofrece una vía eficiente para obtener valiosos compuestos de carbonilo no saturados alquinilados enriquecidos con enantio.
  • La utilidad sintética se valida a través de la ampliación y la aplicación a la síntesis de moléculas complejas.