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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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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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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Mecanismo y alcance de la borilación descarbonizante catalizada por níquel de los fluoruros de ácido carboxílico

Christian A Malapit1, James R Bour1, Simon R Laursen1

  • 1Department of Chemistry , University of Michigan , 930 North University Avenue , Ann Arbor , Michigan 48109 , United States.

Journal of the American Chemical Society
|October 17, 2019
PubMed
Resumen

Una nueva reacción catalizada por níquel convierte eficientemente los fluoruros de ácido carboxílico en ésteres de boronato de arilo utilizando reactivos de diboro. Este método libre de bases ofrece una ruta simplificada para sintetizar compuestos de boro valiosos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis
  • Química del organoboron

Sus antecedentes:

  • Los derivados del ácido carboxílico son precursores sintéticos versátiles.
  • Los ésteres de boronato de arilo son componentes cruciales en la síntesis orgánica.
  • El desarrollo de métodos catalíticos eficientes para la formación de enlaces C-B es un área de investigación activa.

Objetivo del estudio:

  • Desarrollar una nueva reacción de acoplamiento descarbonizante catalizada por níquel sin bases.
  • Para sintetizar ésteres de boronato de arilo a partir de fluoruros de ácido carboxílico y reactivos de diboro.
  • Para aclarar el mecanismo de reacción y optimizar las condiciones catalíticas.

Principales métodos:

  • Acoplamiento descarbonizado catalizado por níquel.
  • Estudios mecanicistas que incluyen evaluaciones de la tasa de transmitación.
  • Optimización de los parámetros de reacción, incluidos los catalizadores y los reactivos.
  • Generación in situ de fluoruros ácidos a partir de ácidos carboxílicos.

Principales resultados:

  • Formación selectiva de ésteres de boronato de arilo a partir de fluoruros de ácido carboxílico y reactivos de diboron.
  • Se ha demostrado que los reactivos de diboro se transmiten más rápidamente que los ésteres de boronato de arilo con un intermediario de Ni (arilo) (fluoruro).
  • La reactividad se correlaciona con la electrofilicidad del centro de boro.
  • Aplicabilidad a varios fluoruros de ácido (hetero) arilo carboxílico y reactivos de diboro.
  • Identificación de los precatalizadores de níquel estables al aire.

Conclusiones:

  • Se ha desarrollado una nueva y eficiente borilación descarbonizada catalizada por níquel de fluoruros ácidos.
  • Las ideas mecanicistas guiaron la optimización y expansión del alcance de la reacción.
  • El método proporciona una vía práctica para los ésteres de boronato de arilo, con potencial para la generación in situ de materiales de partida.