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La orto-alilación catalizada por el hierro de carboxamidas aromáticas con éteres de alilo

Sobi Asako¹, Laurean Ilies, Eiichi Nakamura

¹Department of Chemistry, School of Science, The University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|November 13, 2013

Resumen

Los catalizadores de hierro permiten la orto-alilación de arenas utilizando el éter de allilfenilo. Este método de activación C-H ofrece una nueva ruta para la síntesis de valiosos compuestos orgánicos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Dirigir la funcionalización C-H asistida por el grupo es una herramienta poderosa en la síntesis orgánica.
La catálisis del hierro ofrece una alternativa rentable y sostenible a los catalizadores de metales preciosos.

Objetivo del estudio:

Desarrollar una nueva orto-alilación catalizada por hierro de arenas utilizando grupos directivos de N- ((quinolina-8-il) amida.
Para explorar el mecanismo de la activación C-H y la posterior alilación.

Principales métodos:

Empleando un sistema de catalizador de hierro y difosfina.
Utilizando una base organometálica para la reacción.
Arenas que reaccionan con el éter de fenilo-alilo a 50-70 °C.

Principales resultados:

Se logró una eficiente orto-alianza de las arenas.
La reacción procede a través de la activación C-H catalizada por el hierro.
Se observó una alilación γ-selectiva del intermediario de hierro con éter de fenilo alílico.

Conclusiones:

Se ha establecido un nuevo y eficiente método de ortoalilación catalizada por hierro.
La metodología proporciona una valiosa ruta sintética para arenas funcionalizadas.
El estudio destaca el potencial de la catálisis del hierro en las estrategias de activación de C-H.

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