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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 confirmed through isotopic...
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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.
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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 the...
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Friedel–Crafts reactions were developed in 1877 by the French chemist Charles Friedel and the American chemist James Crafts. Friedel–Crafts alkylation refers to the replacement of an aromatic proton with an alkyl group via electrophilic aromatic substitution. A Lewis acid catalyst such as aluminum chloride reacts with an alkyl halide to form a carbocation. The resulting carbocation then reacts with the aromatic ring and undergoes a series of electron rearrangements before giving the final...
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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...

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Una reacción aromática de Glaser-Hay.

Hien-Quang Do1, Olafs Daugulis

  • 1Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

Journal of the American Chemical Society
|November 11, 2009
PubMed
Resumen

Un nuevo método catalizado por el cobre permite la dimerización deprotonativa de arenas utilizando oxígeno como oxidante. Esta reacción versátil funciona para varios compuestos aromáticos ricos en electrones y pobres en electrones, tolerando diversos grupos funcionales.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • La catálisis de la catálisis.
  • Metodología sintética de la metodología sintética.

Sus antecedentes:

  • La funcionalización de arenas es crucial en la síntesis orgánica.
  • El desarrollo de métodos eficientes y selectivos para la activación y acoplamiento de enlaces C-H es un desafío clave.
  • La catálisis del cobre ofrece un enfoque sostenible y rentable para las transformaciones orgánicas.

Objetivo del estudio:

  • Desarrollar un método general y eficiente para la dimerización deprotonativa catalizada por cobre de arenas.
  • Para utilizar el oxígeno como un oxidante terminal verde para las reacciones de acoplamiento de areno.
  • Para explorar el alcance del sustrato y la tolerancia del grupo funcional del método desarrollado.

Principales métodos:

  • Reacción catalizada por el cobre.
  • La dimerización deprotonativa de las arenas.
  • Utilizando oxígeno molecular como el oxidante terminal.
  • Cribado de catalizadores, ligandos y condiciones de reacción.

Principales resultados:

  • Se estableció un método general para la dimerización deprotonativa catalizada por cobre de las arenas.
  • La reacción acopla efectivamente los heterociclos ricos en electrones y los heterociclos pobres en electrones, así como las arenas pobres en electrones.
  • La metodología desarrollada demuestra tolerancia hacia varios grupos funcionales, incluidos los grupos nitro, ciano, dialquilamino y éster.
  • El oxígeno se empleó con éxito como oxidante terminal, destacando el aspecto verde de la reacción.

Conclusiones:

  • Se ha desarrollado con éxito una nueva y versátil dimerización deprotonativa catalizada por cobre de arenas.
  • El método ofrece un enfoque sostenible utilizando oxígeno como oxidante y exhibe un amplio alcance de sustrato y tolerancia de grupo funcional.
  • Este trabajo proporciona una herramienta valiosa para la síntesis de compuestos aromáticos complejos a través de la activación y dimerización de C-H.