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Hidroaminación intermolecular de 1,3-dienos catalizados por complejos bis ((fosfina) carbodicarbeno-rodío

Matthew J Goldfogel¹, Courtney C Roberts, Simon J Meek

¹Department of Chemistry, The University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599-3290, United States.

Journal of the American Chemical Society

|April 19, 2014

Resumen

Los investigadores desarrollaron un nuevo ligando de pinza de carbodicarbeno (CDC) para la hidroaminación catalizada por Rh (I) de dienes. Este eficiente sistema catalítico produce aminas alilicas con alta selectividad.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los ligandos de la pinza son cruciales en la catálisis homogénea.
Los ligandos de carbodicarbeno (CDC) ofrecen propiedades electrónicas y estéricas únicas.
Las reacciones de hidroaminación son importantes para la síntesis de aminas.

Objetivo del estudio:

Para informar sobre un nuevo andamio de ligando de pinza basado en carbodicarbeno (CDC).
Para demostrar su aplicación en la hidroaminación intermolecular catalizada por Rh (I) de 1,3-dienes.
Establecer complejos de CDC como catalizadores eficientes para esta transformación.

Principales métodos:

Síntesis de un andamio de ligando de pinza basado en el CDC.
Hidroaminación intermolecular catalizada por Rh (I) de 1,3-dienos con aminas arilo y alquilo.
Optimización de las condiciones de reacción (carga del catalizador, temperatura).

Principales resultados:

El primer ejemplo de un complejo de CDC bien definido utilizado como un catalizador eficiente.
Altos rendimientos (hasta el 97%) de aminas alilicas.
Se logró una excelente selectividad del sitio (> 98: 2).

Conclusiones:

Los ligandos de pinza basados en los CDC son catalizadores efectivos para la hidroaminación.
Esta metodología proporciona una ruta selectiva del sitio a las aminas alilicas.
El sistema catalítico desarrollado ofrece una herramienta valiosa en la síntesis orgánica.

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