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El acoplamiento biarílico deshidrogenado cruzado de catálisis dual cooperativa Au/Ag: desarrollo de la reacción y

Weipeng Li¹, Dandan Yuan², Guoqiang Wang²

¹State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering , Nanjing University , Nanjing 210023 , China.

Journal of the American Chemical Society

|January 26, 2019

Resumen

Una nueva reacción catalizada por oro y plata permite un acoplamiento biarílico eficiente entre pirazoles y fluoroarenos. Este estudio revela que el acetato de plata es el catalizador clave para la activación de C-H, lo que lleva a nuevos compuestos de biheteroarilo.

Área de la Ciencia:

Química orgánica
Catálisis
Química Heterocíclica

Sus antecedentes:

La catálisis del oro y la plata son vitales en la síntesis orgánica.
Las reacciones de acoplamiento deshidrogenativo cruzado ofrecen una formación eficiente de enlaces.
A menudo se pasa por alto el papel de la plata en las reacciones catalizadas por el oro.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento de biarilo deshidrogenado cruzado catalizado por Au/Ag bimetálico.
Para investigar el papel catalítico de las sales de plata en las transformaciones catalizadas por el oro.
Para sintetizar una amplia gama de productos de biheteroarilo.

Principales métodos:

Utilizó un sistema catalítico bimetálico de oro y plata.
Se utiliza el acoplamiento deshidrogenativo cruzado entre pirazoles y fluoroarenos.
Se han realizado estudios experimentales y teóricos para elucidar el mecanismo catalítico.

Principales resultados:

Se logró una reacción de acoplamiento de biarilo altamente selectiva y operacionalmente simple.
Se obtiene una amplia gama de productos de biheteroarilo con rendimientos de moderados a buenos.
Demostró una excelente compatibilidad de grupo funcional.
Acetato de plata identificado como el catalizador activo para la activación C-H de los fluoroarenos.

Conclusiones:

Propuso un mecanismo de catálisis dual Au/Ag sin precedentes.
La plata (I) activa los fluoroarenos mediante una metalización-desprotonación concertada.
El oro (III) activa los pirazoles a través de la sustitución aromática electrofílica.
La activación C-H de los pirazoles por ArFnAu (III) es el paso que limita la velocidad.

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