Search research articles

ACERCA DE JoVE

Visión General Liderazgo Blog Centro de Ayuda JoVE

AUTORES

Proceso de Publicación Consejo Editorial Alcance y Políticas Revisión por Pares Preguntas Frecuentes Enviar

BIBLIOTECARIOS

Testimonios Suscripciones Acceso Recursos Consejo Asesor de Bibliotecas Preguntas Frecuentes

INVESTIGACIÓN

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archivo

EDUCACIÓN

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Centro de Recursos para Profesores Sitio de Profesores

Términos y Condiciones de Uso

Política de Privacidad

Videos de Conceptos Relacionados

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Nucleophilic Aromatic Substitution: Elimination–Addition

Nucleophilic Aromatic Substitution: Elimination–Addition

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...

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

Nucleophilic Aromatic Substitution: Addition–Elimination (S_NAr)

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...

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

También podría leer

Artículos Relacionados

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

Ordenar por

Same author

Enantioselective Radical Cascade Cyclization to Axially Chiral Medium-Sized Lactones.

Angewandte Chemie (International ed. in English)·2026

Same author

Ligand-Regulated Metallaphotoredox Aminoarylation for the Valorization of Feedstock Alkenes.

Journal of the American Chemical Society·2026

Same author

<i>meta</i>-Chloroperbenzoic-Acid-Promoted Oxidative Annulations of Alkynes and Nitriles into Oxazoles via Putative β-Hydroxy Vinyl Cations.

Organic letters·2026

Same author

Overriding the radical polarity matching principle: selective chlorohydroxylation of electron-deficient alkenes enabled by Ce photocatalysis.

Chemical science·2026

Same author

Theoretical Study and Rational Design of Noncovalent Interactions Enable Organocatalytic Divergent [2+2] and [4+2] Annulations.

Organic letters·2026

Same author

Enantioselective Synthesis of Isoquinuclidine Analogs by Synergistic Copper/Amine-Catalyzed Sequential [3 + 3]/[4 + 2] Cycloaddition.

Angewandte Chemie (International ed. in English)·2026

Search research articles

Video Experimental Relacionado

Updated: Dec 7, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Anulación C-F/N-H catalizada por níquel de amidas aromáticas con alquinas: activación de enlaces C-F bajo condiciones

Itsuki Nohira¹, Song Liu², Ruopeng Bai²

¹Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Journal of the American Chemical Society

|September 28, 2020

Resumen

Este estudio introduce una nueva reacción catalizada por el níquel que forma isoinolinonas 1 ((2H) por anulación C-F/N-H. El proceso eficiente utiliza condiciones suaves y bases débiles, ofreciendo una nueva ruta sintética.

Más Videos Relacionados

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

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

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

Published on: June 21, 2017

Videos de Experimentos Relacionados

Last Updated: Dec 7, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

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

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

Published on: June 21, 2017

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las amidas aromáticas con sustituyentes ortofluoro son precursores sintéticos valiosos.
El desarrollo de métodos catalíticos eficientes para la funcionalización de enlaces C-F sigue siendo un desafío importante en la síntesis orgánica.

Objetivo del estudio:

Desarrollar una nueva reacción de anulación catalizada por níquel para la síntesis de isoquinolinonas 1 ((2H).
Explorar la anulación C-F/N-H de las amidas aromáticas sustituidas por ortofluoro con alquinas.

Principales métodos:

Reacción catalizada por níquel de amidas aromáticas sustituidas por ortofluoro con las alquinas.
Se utiliza terciobutoxido de potasio (KOtBu) o carbonato de cesio (Cs2CO3) como base.
Reacciones realizadas en condiciones suaves (40-60 °C) sin ligandos.
Se emplearon cálculos de la Teoría Funcional de la Densidad (DFT) para dilucidar el mecanismo de reacción.

Principales resultados:

Se han sintetizado con éxito derivados de la isoquinolinona 1 ((2H) a través de una vía de anulación C-F/N-H.
La reacción es efectiva con bases débiles y procede eficientemente sin la necesidad de ligandos.
Las temperaturas de reacción suaves (40-60 °C) fueron suficientes para obtener altos rendimientos.

Conclusiones:

La reacción catalizada por Ni desarrollada proporciona una ruta eficiente y suave a las 1 ((2H) -isoquinolinonas.
La estrategia de anulación C-F/N-H ofrece una nueva herramienta valiosa para los químicos orgánicos sintéticos.
Los cálculos de DFT confirmaron un ciclo catalítico plausible que involucra pasos clave como la adición oxidativa de enlaces C-F y la inserción de alquina.