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Acoplamiento cruzado reductivo entre enlaces C (arilo) -N y C (arilo) -O no activados por catálisis de cromo

Jinghua Tang¹, Fei Fan¹, Xuefeng Cong¹

¹Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.

Journal of the American Chemical Society

|June 27, 2020

Resumen

Este estudio introduce la catálisis por cromo para el acoplamiento cruzado reductivo de enlaces arilo-nitrógeno y arilo-oxígeno no activados. Este método forma eficientemente nuevos enlaces carbono-carbono a partir de enlaces químicos previamente inertes.

Área de la Ciencia:

Química orgánica
Catálisis
Química sintética

Sus antecedentes:

Los enlaces químicamente inertes presentan desafíos significativos en la química sintética.
El desarrollo de métodos para el acoplamiento reductivo de enlaces no activados es crucial para una síntesis eficiente.

Objetivo del estudio:

Para reportar una nueva reacción de acoplamiento cruzado catalizado por cromo.
Para acoplar enlaces arilo-nitrógeno y arilo-oxígeno no activados.

Principales métodos:

Se utiliza el cloruro de cromo (CrCl2) como catalizador.
Utilizó un ligando bipirídico y magnesio como reductor.
Mecanismos de reacción investigados mediante experimentos de etiquetado con deuterio.

Principales resultados:

Se ha logrado un acoplamiento reductivo exitoso entre los enlaces no activados C (arilo) -N y C (arilo) -O.
Se ha demostrado una alta reactividad y la formación de enlaces C (arilo) -C (arilo).
Identificación de la escisión preferencial de los enlaces C (arilo) -N en los derivados de la anilina.

Conclusiones:

La catálisis por cromo ofrece una estrategia eficaz para el acoplamiento cruzado reductivo de enlaces inertes.
El método desarrollado proporciona una nueva ruta para la formación de enlaces C-C.
Los conocimientos mecanicistas sugieren un modelo de coordinación bipiridil-cromo 1:1.

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