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El acoplamiento Suzuki-Miyaura de nitroarenos

M Ramu Yadav¹, Masahiro Nagaoka¹, Myuto Kashihara¹

¹Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.

Journal of the American Chemical Society

|July 6, 2017

Resumen

Este estudio introduce un nuevo método de acoplamiento Suzuki-Miyaura que utiliza nitroarenos para la síntesis de biarilo. La catálisis del paladio inicia la reacción mediante la escisión del enlace arilo-nitro, un paso previamente desconocido.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

El acoplamiento Suzuki-Miyaura es una reacción vital para la formación de enlaces carbono-carbono.
El acoplamiento tradicional Suzuki-Miyaura a menudo requiere sustratos prefuncionalizados.
Los nitroarenos están fácilmente disponibles pero son socios electrófilos difíciles.

Objetivo del estudio:

Para desarrollar una nueva vía sintética para los compuestos de biarilo.
Para utilizar los nitroarenos como socios electrófilos en el acoplamiento Suzuki-Miyaura.
Para aclarar el mecanismo de esta nueva transformación.

Principales métodos:

Reacción de acoplamiento Suzuki-Miyaura catalizada por el paladio.
Utilización de nitroarenos como socios de acoplamiento electrófilo.
Investigaciones mecanicistas detalladas.

Principales resultados:

Síntesis exitosa de biarilos mediante el uso de nitroarenos.
Identificación de la escisión del enlace arilo-nitro por el paladio como el paso inicial.
Demostración de una reacción elemental sin precedentes en el ciclo catalítico.

Conclusiones:

Los nitroarenos pueden servir como socios electrófilos efectivos en el acoplamiento Suzuki-Miyaura.
La escisión del enlace aril-nitro mediada por el paladio es un paso clave y nuevo.
Este trabajo amplía el alcance de las reacciones de acoplamiento Suzuki-Miyaura.

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