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Videos de Conceptos Relacionados

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.2K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

11.2K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
11.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

8.5K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
8.5K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.1K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Funcionalización de C-H vinílico catalizado con electroquímica habilitada

Qi-Liang Yang1,2, Yi-Kang Xing1, Xiang-Yang Wang1

  • 1State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.

Journal of the American Chemical Society
|November 13, 2019
PubMed
Resumen

Este estudio introduce la funcionalización electroquímica de C-H vinílico mediante catálisis de iridio para la anulación de alquinos. El método produce eficientemente α-pironas valiosas a partir de ácidos acrílicos y alquinas.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • La electroquímica

Sus antecedentes:

  • La funcionalización C-H selectiva del sitio es crucial en la síntesis orgánica.
  • La catálisis organometálica y la electroquímica ofrecen poderosos enfoques sinérgicos.
  • Los métodos actuales se centran predominantemente en la funcionalización del areno C-H.

Objetivo del estudio:

  • Desarrollar un nuevo método electroquímico para la funcionalización del C-H vinílico.
  • Para lograr la anulación selectiva del sitio de los ácidos acrílicos con alquinas.
  • Para sintetizar las α-pironas mediante una combinación de electroquímica y catálisis de iridio.

Principales métodos:

  • Oxidación electroquímica en una célula no dividida.
  • Utilizando un catalizador de iridio para la funcionalización C-H/O-H.
  • Reacción de los ácidos acrílicos con las alquinas.

Principales resultados:

  • Síntesis eficiente de α-pironas con rendimientos de buenos a excelentes.
  • Demostración de la funcionalidad electroquímica vinílica C-H, expandiéndose más allá de las arenas.
  • Oxidación anódica identificada como crítica para la liberación del producto y la regeneración del catalizador.
  • Comparación con los oxidantes químicos que muestran la necesidad de corriente eléctrica.

Conclusiones:

  • La funcionalización electroquímica del vinilo C-H es una estrategia sintética viable y eficiente.
  • El método desarrollado proporciona una nueva vía para las α-pironas.
  • El enfoque sinérgico electro-organometálico supera las limitaciones de los métodos anteriores.