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α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

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Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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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.
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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...
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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Halogenación C-H habilitada por ligandos de los ácidos (hetero) benzoico y (hetero) acrílico

Haiwei Zhao1, Zhen Li1, Xinyu Zhu1

  • 1Department of Chemistry, The Scripps Research Institute, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|August 22, 2025
PubMed
Resumen
Este resumen es generado por máquina.

Un nuevo método catalítico de halogenación C-H utilizando nuevos ligandos de piridona permite la síntesis práctica de arenas ortohalogenadas. Este enfoque supera las limitaciones de los métodos anteriores, ofreciendo una ruta escalable y eficiente a valiosos intermedios para el descubrimiento de fármacos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química medicinal

Sus antecedentes:

  • Las arenas ortohalogenadas son bloques de construcción cruciales en las reacciones de acoplamiento cruzado.
  • La síntesis tradicional se basa en la ortolitización / halogenación estequiométrica, que tiene escalabilidad y desventajas ambientales.
  • Los métodos de halogenación catalítica C-H existentes se enfrentan a limitaciones que incluyen el requisito de bases estequiométricas, oxidantes caros, grupos de dirección y incompatibilidad con los heterociclos.

Objetivo del estudio:

  • Desarrollar un método práctico y escalable de halogenación catalítica de C-H para las arenas ortohalogenadas.
  • Superar las limitaciones de las técnicas de halogenación catalítica C-H existentes, especialmente para aplicaciones químicas medicinales.
  • Para permitir la síntesis eficiente de productos intermedios avanzados para moléculas de fármacos.

Principales métodos:

  • Desarrollo de tres nuevos ligandos de piridona bifuncional.
  • Utilizando un catalizador de paládio con ligando para la halogenación de C-H.
  • Utilizando reactivos halogenados industriales de bajo costo (NXS) y acetonitrilo como disolvente.

Principales resultados:

  • El método desarrollado elimina efectivamente la necesidad de bases estequiométricas, oxidantes caros y grupos de dirección.
  • Se superó la incompatibilidad de la halogenación C-H catalizada por Pd (II) sin ligandos con sustratos heterocíclicos.
  • La nueva tecnología de halogenación C-H es práctica y escalable, utilizando reactivos y condiciones fácilmente disponibles.
  • Síntesis demostrada en un solo paso de fármacos intermedios avanzados que anteriormente requerían múltiples pasos.

Conclusiones:

  • El descubrimiento de ligandos bifuncionales de piridona bidentada ha hecho que la tecnología de halogenación C-H sea significativamente más práctica.
  • Este enfoque catalítico proporciona una alternativa eficiente y escalable a los métodos tradicionales para sintetizar arenas ortohalogenadas.
  • El método facilita el acceso simplificado a productos intermedios complejos vitales para la química medicinal y el desarrollo de fármacos.