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Clivado reductor catalizado por rutenio de enlaces arilo-arilo no tensados: desarrollo de la reacción y estudio

Jun Zhu¹, Peng-Hao Chen², Gang Lu^3,4

¹Department of Chemistry , University of Chicago , Chicago , Illinois 60637 , United States.

Journal of the American Chemical Society

|November 2, 2019

Resumen

Los investigadores desarrollaron un nuevo método catalizado por rutenio para la escisión de enlaces arilo-arilo duros. Este avance permite nuevas vías sintéticas y tolera varios grupos funcionales, ofreciendo una amplia aplicabilidad en la síntesis orgánica.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La escisión del enlace carbono-carbono es crucial en procesos industriales como el craqueo del petróleo.
La activación de enlaces arilo-arilo no tensados y no polares sigue siendo un desafío importante en la química sintética.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por rutenio para la escisión reductiva de enlaces C (arilo) -C (arilo) no tensados.
Explorar el alcance y las limitaciones de esta nueva reacción.
Para aclarar el mecanismo de reacción.

Principales métodos:

Clivado reductor catalizado por rutenio de compuestos de biarilo.
Se utilizan grupos de dirección (DGs) como la piridina, la quinolina, la pirimidina y el pirazol.
Se emplean varios reductores terminales, incluido el gas hidrógeno, el éster de Hantzsch, los silanos y los alcoholes.

Principales resultados:

Se ha escindido con éxito una amplia gama de enlaces C ((arilo) -C ((arilo) no tensados en compuestos biarílicos con grupos direccionales.
Tolerancia demostrada a numerosos grupos funcionales debido a las condiciones de pH neutro y libre de oxidantes.
Se logró una reacción de activación y acoplamiento C-C de un solo recipiente.
Se ha identificado el ciclo catalítico que implica un intermediario de monohidruro de rutenio y un dicloruro de rutenio coordinado con η4.

Conclusiones:

Desarrolló un clivado reductor catalizado por Ru de enlaces arilo-C arilo desafiantes.
El método ofrece un amplio alcance de sustrato y tolerancia de grupo funcional.
Las ideas mecanicistas proporcionan una base para futuras transformaciones catalíticas.

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