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

Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

7.0K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
7.0K
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

10.3K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
10.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.9K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
19.9K
Preparation of Alcohols via Substitution Reactions01:38

Preparation of Alcohols via Substitution Reactions

6.9K
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...
6.9K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.6K
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.
8.6K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.1K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.1K

También podría leer

Artículos Relacionados

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

Ordenar por
Same author

Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.

Journal of the American Chemical Society·2026
Same author

Enantioconvergent Decarboxylative Arylation of Serine and Isoserine Derivatives with Aryl Halides: Modular Access to Chiral 1,2-Amino Alcohols.

Journal of the American Chemical Society·2026
Same author

Tumor-induced species-specific dysbiosis drives renal innate immunity and nephrogenic ascites.

bioRxiv : the preprint server for biology·2026
Same author

An Integrated <sup>12</sup>C/<sup>13</sup>C Exchange Platform for Accessing Isotopically-Labeled Ketones via Dual Catalytic C-C Bond-Functionalization.

ACS catalysis·2026
Same author

Dual Catalytic Enantioconvergent Carbamoylation of Aziridines.

Journal of the American Chemical Society·2025
Same author

Regiodivergent Deuteration of Pyridine-Based Heterocycles.

Organic letters·2025

Video Experimental Relacionado

Updated: Nov 28, 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

8.2K

Estrategia catalítica dual para forjar arquitecturas sp2 y sp3 a través de la escisión de derivados de alcohol

Fei Cong1,2, Xin-Yang Lv1,2, Craig S Day1,2

  • 1Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Avenida Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society
|November 30, 2020
PubMed
Resumen

Este estudio introduce una plataforma catalítica dual para la creación de enlaces de carbono sp2-sp3 y sp3-sp3. El método funciona de manera eficiente las moléculas utilizando derivados de alcohol y haluros, aplicables incluso en la síntesis de última etapa.

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

13.3K
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

7.2K

Videos de Experimentos Relacionados

Last Updated: Nov 28, 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

8.2K
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

13.3K
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

7.2K

Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • La formación de enlaces carbono-carbono es fundamental en la síntesis orgánica.
  • El desarrollo de métodos versátiles para crear enlaces sp2-sp3 y sp3-sp3 sigue siendo un desafío clave.
  • La funcionalización en etapa tardía requiere protocolos sintéticos robustos y ampliamente aplicables.

Objetivo del estudio:

  • Para revelar una plataforma dual para forjar enlaces de carbono sp2-sp3 y sp3-sp3.
  • Para permitir la síntesis de moléculas orgánicas complejas a través de la formación de enlaces catalíticos C-C.
  • Demostrar la utilidad del método en la fase final de la funcionalidad.

Principales métodos:

  • Disolución por catalización de los derivados del alcohol alifático.
  • Acoplamiento de derivados alcohólicos con haluros de arilo y alquilo.
  • Utilizando una plataforma dual para distintas formaciones de enlace C-C.

Principales resultados:

  • Formación exitosa de enlaces de carbono sp2-sp3 y sp3-sp3.
  • Demostrado amplio alcance del sustrato para el protocolo desarrollado.
  • Se ha demostrado una amplia aplicabilidad, incluso en escenarios de funcionalización en etapas avanzadas.

Conclusiones:

  • La plataforma dual revelada ofrece una nueva y poderosa herramienta para la síntesis orgánica.
  • El método proporciona un acceso eficiente a los valiosos enlaces de carbono sp2-sp3 y sp3-sp3.
  • Este enfoque avanza significativamente las capacidades para la funcionalización en etapa tardía de moléculas complejas.