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Hidroaminación intramolecular catalizada por platino de olefinas no activadas con alquilaminas secundarias

Christopher F Bender¹, Ross A Widenhoefer

¹P M Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.

Journal of the American Chemical Society

|January 27, 2005

Resumen

Este estudio demuestra una nueva hidroaminación intramolecular catalizada por platino de las aminoolefinas, sintetizando eficientemente los derivados de la pirrolidina. La reacción muestra una excelente tolerancia del grupo funcional y una baja sensibilidad a la humedad, ofreciendo una vía sintética versátil.

Área de la Ciencia:

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

Sus antecedentes:

La hidroaminación intramolecular es una reacción clave para sintetizar heterociclos que contienen nitrógeno.
El desarrollo de sistemas catalíticos eficientes y selectivos para la hidroaminación sigue siendo un área activa de investigación.

Objetivo del estudio:

Para explorar la utilidad de un catalizador de platino para la hidroaminación intramolecular de las olefinas gamma y delta-amino.
Para sintetizar derivados de pirrolidina con altos rendimientos y compatibilidad de grupo funcional.

Principales métodos:

Reacción de la bencil-2,2-difenil-4-pentenilamina con una mezcla catalítica de [PtCl2(H2C=CH2) ]2 y trifenilfosfina (PPh3).
Calentar la mezcla de reacción en dioxano a 120°C durante 16 horas.
Aislamiento y caracterización del producto de pirrolidina.

Principales resultados:

La reacción produjo con éxito 1-benzil-2-metil-4,4-difenilpirrolidina con un rendimiento del 75%.
Una gama de olefinas gamma y delta-amino se convirtió en derivados de pirrolidina en rendimientos de moderados a buenos.
El sistema catalítico exhibió una excelente compatibilidad de grupos funcionales y una baja sensibilidad a la humedad.

Conclusiones:

La hidroaminación intramolecular catalizada por platino proporciona una ruta efectiva hacia las pirrolidinas sustituidas.
El método desarrollado es robusto, versátil y tolerante de varios grupos funcionales.
Esta metodología ofrece una herramienta valiosa para la síntesis de heterociclos de nitrógeno.

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