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Dimerización alquilativa ni-catalizada de reactivos de vinilo grignard utilizando fluoruros de alquilo
Jun Terao1, Hiroyasu Watabe, Nobuaki Kambe
1Department of Molecular Chemistry & Science and Technology Center for Atoms, Molecules and Ions Control, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
Journal of the American Chemical Society
|March 18, 2005
Resumen
Los fluoruros de alquilo primarios y secundarios reaccionan con el cloruro de vinilmagnesio utilizando un catalizador de níquel para formar reactivos de 2-alquilo-3-butenilo Grignard. Los fluoruros de alquilo son agentes alquiladores superiores en esta reacción única de acoplamiento cruzado.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química organometálica Química orgánica de los metales.
Sus antecedentes:
- Las reacciones de acoplamiento cruzado son vitales en la síntesis orgánica.
- Las reacciones catalizadas por níquel ofrecen rutas sintéticas eficientes.
- Los reactivos de Grignard son unos versátiles intermedios organometálicos.
Objetivo del estudio:
- Para investigar una nueva reacción de acoplamiento cruzado entre haluros de alquilo y cloruro de vinilo magnesio.
- Explorar la utilidad de los fluoruros de alquilo como agentes alquiladores en reacciones catalizadas por níquel.
- Para sintetizar los reactivos 2-alquilo-3-butenilo de Grignard.
Principales métodos:
- Reacción de haluros de alquilo (específicamente fluoruros de alquilo primarios y secundarios) con cloruro de vinilo magnesio.
- Utilizando un catalizador de níquel en tetrahidrofurano (THF) a 25 grados C.
- Análisis de los productos de reacción, incluida la formación del reactivo de Grignard 2-alquilo-3-butenilo (1) y el producto de acoplamiento de vinilo doble alquilado (4).
Principales resultados:
- Se obtuvieron altos rendimientos del reactivo Grignard 2-alquilo-3-butenilo (1) utilizando fluoruros de alquilo primarios y secundarios.
- La reacción procedió eficientemente a temperatura ambiente (25 grados C).
- Los fluoruros de alquilo demostraron un rendimiento superior como agentes alquiladores en comparación con los cloruros, bromuros y yoduros en este acoplamiento específico.
Conclusiones:
- Se ha desarrollado una reacción única y eficiente de acoplamiento cruzado catalizado por níquel entre haluros de alquilo y cloruro de vinilmagnesio.
- Los fluoruros de alquilo primarios y secundarios son agentes alquiladores muy eficaces para la síntesis de reactivos 2-alquilo-3-butenilo Grignard.
- Este método proporciona una valiosa ruta a los reactivos de Grignard funcionalizados con aplicaciones potenciales en la síntesis orgánica.
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