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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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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...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

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Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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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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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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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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In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.
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Funcionalización de C-H aromático selectivo y versátil por tiantrenación

Florian Berger1, Matthew B Plutschack1, Julian Riegger1

  • 1Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany.

Nature
|March 15, 2019
PubMed
Resumen
Este resumen es generado por máquina.

Los investigadores desarrollaron un nuevo método de funcionalización aromática de C-H utilizando un radical de azufre. Este enfoque logra una alta selectividad sin dirigir grupos, lo que permite la síntesis de diversos derivados.

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Área de la Ciencia:

  • Química orgánica
  • Química sintética

Sus antecedentes:

  • La funcionalización directa C-H mejora la complejidad molecular, pero a menudo carece de selectividad del sitio.
  • Los métodos existentes generalmente requieren grupos de dirección o patrones de sustitución específicos para la regioselectividad.
  • La funcionalización aromática C-H generalmente produce múltiples isómeros del producto sin dicha guía.

Objetivo del estudio:

  • Desarrollar una reacción de funcionalización aromática C-H altamente selectiva.
  • Permitir la síntesis de derivados de areno bien definidos sin depender de grupos de dirección.
  • Para proporcionar arenas funcionales susceptibles a nuevas transformaciones sintéticas.

Principales métodos:

  • Introducción de un radical persistente basado en azufre para la funcionalización del areno.
  • Aplicación de la catálisis de metales de transición y de la fotorreducción.
  • Utilizando sales de tiantenio como intermediarios versátiles.

Principales resultados:

  • Se logra una alta selectividad posicional en la funcionalización aromática C-H sin grupos de dirección.
  • Funcionalizó con éxito arenas complejas, produciendo sales de tiantenio.
  • Demostró la utilidad de los productos en diversas transformaciones químicas posteriores.

Conclusiones:

  • Desarrolló un método de funcionalización aromática C-H fundamentalmente nuevo.
  • Proporciona acceso directo a una amplia gama de derivados complejos de moléculas pequeñas.
  • Ofrece una selectividad sin precedentes para generar diversidad funcional en las arenas.