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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Acoplamiento de nitrógeno y hidrocarburos a través de la migración de arilo

Sean F McWilliams¹, Daniël L J Broere^1,2, Connor J V Halliday³

¹Department of Chemistry, Yale University, New Haven, CT, USA.

|August 14, 2020

Resumen

Los investigadores desarrollaron un sistema catalizador de hierro que activa los abundantes hidrocarburos y el nitrógeno atmosférico (N2) para crear derivados de la anilina. Este avance permite el acoplamiento directo de N2 con hidrocarburos, allanando el camino para nuevos métodos catalíticos.

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Área de la Ciencia:

* Química inorgánica
* Catálisis
* Química organometálica

Sus antecedentes:

* La activación de moléculas inertes como los hidrocarburos y el nitrógeno atmosférico (N₂) es un desafío significativo en la química.
* Los métodos tradicionales para formar enlaces carbono-nitrógeno a partir de N2 requieren precursores orgánicos reactivos incompatibles con las condiciones reductivas necesarias para la activación de N2, lo que dificulta las aplicaciones catalíticas.

Objetivo del estudio:

* Informar de un nuevo sistema de hierro soportado por diketiminato capaz de activar secuencialmente el benceno y el N2.
* Para demostrar una conversión de arenas derivadas del petróleo en derivados de anilina sililados utilizando N2 como fuente de nitrógeno.

Principales métodos:

* Utilizó un complejo de bromuro de hierro soportado por diketiminato.
* Utilizó una mezcla de reacción que incluía polvo de sodio, éter de corona, bromuro de trimetilsililo y N₂.
* Compuestos intermedios aislados y caracterizados en la vía de reacción.

Principales resultados:

* Acoplado con éxito benceno y N2 para formar derivados de anilina a través de un mecanismo de activación secuencial.
* Se ha conseguido una conversión en un solo recipiente de varios arenes en anilinas sililadas.
* Se han identificado y caracterizado los principales intermediarios que respaldan un mecanismo de reacción propuesto.

Conclusiones:

* El sistema de hierro desarrollado permite el acoplamiento directo del nitrógeno atmosférico con los abundantes hidrocarburos.
Esta estrategia ofrece una nueva vía para la síntesis de derivados de anilina y avanza en el desarrollo de sistemas catalíticos para la funcionalización de N2.