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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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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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The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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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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Diseño de un ligando benzonitrílico que extrae electrones para el acoplamiento cruzado catalizado por Ni con

L Reginald Mills1, Racquel K Edjoc1, Sophie A L Rousseaux1

  • 1Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada.

Journal of the American Chemical Society
|July 1, 2021
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Los investigadores desarrollaron un nuevo ligando benzonitrilo para reacciones de acoplamiento cruzado catalizadas por níquel. Este ligando promueve una arilación eficiente, lo que permite la síntesis de valiosos α-arilnitriles cuaternarios a partir de malononitriles.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Metodología sintética

Sus antecedentes:

  • El desarrollo de nuevos ligandos es crucial para el avance de las reacciones de acoplamiento cruzado.
  • La catálisis del níquel ofrece una plataforma versátil para sintetizar moléculas orgánicas complejas.
  • Los nucleófilos terciarios presentan desafíos únicos en las reacciones de acoplamiento cruzado.

Objetivo del estudio:

  • Diseñar y sintetizar un nuevo ligando que contenga benzonitrilo para el acoplamiento cruzado catalizado por níquel.
  • Investigar el mecanismo por el cual el ligando influye en el ciclo catalítico.
  • Establecer un nuevo protocolo para la síntesis de los α-arilnitriles cuaternarios.

Principales métodos:

  • Síntesis y caracterización de ligandos.
  • Reacciones de acoplamiento cruzado catalizadas por níquel.
  • Estudios cinéticos y de Hammett para elucidar los mecanismos de reacción.

Principales resultados:

  • Se diseñó y optimizó con éxito un ligando basado en benzonitrilo para la catálisis de Ni.
  • Se encontró que la fracción benzonitrilo actúa como un receptor de electrones, promoviendo la eliminación reductiva.
  • Se desarrolló un nuevo protocolo de descianado-metalización y arilación catalizada por Ni.
  • Se logró el acceso a los α-arilnitriles cuaternarios a partir de malononitriles disueltos.

Conclusiones:

  • El ligando benzonitrilo desarrollado mejora la eficiencia del acoplamiento cruzado catalizado por níquel.
  • Las propiedades electrónicas del ligando son clave para promover las vías de reacción deseadas.
  • Este trabajo proporciona una nueva ruta sintética para valiosos compuestos cuaternarios de α-arilnitrilo.