Sililación carbonilativa cu-catalizada de haluros de alquilo: Acceso eficiente a los acilsilanos
1Department of Chemistry , University of Illinois at Chicago , 845 West Taylor Street , Chicago , Illinois 60607 , United States.
Journal of the American Chemical Society
|December 19, 2019
Resumen
Un nuevo método catalizado por cobre sintetiza eficientemente acilsilanos sustituidos por alquilo a partir de haluros de alquilo no activados. Esta reacción versátil tolera varios grupos funcionales y permite más transformaciones en una olla.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Química del silicio orgánico
Sus antecedentes:
- Los acilsilanos son productos intermedios sintéticos muy valiosos.
- Los métodos eficientes para sintetizar acilsilanos a partir de haluros de alquilo no activados son limitados.
Objetivo del estudio:
- Desarrollar una nueva silición carbonilativa catalizada por el cobre de haluros de alquilo no activados.
- Para sintetizar acilsilanos sustituidos por alquilo de manera eficiente y con una amplia tolerancia de grupo funcional.
Principales métodos:
- Reacción de silición carbonilada catalizada por el cobre.
- Se utilizan haluros de alquilo no activados y agentes silicantes.
- El alcance de la reacción y las vías mecanicistas investigadas.
Principales resultados:
- Se obtienen altos rendimientos de acilsilanos sustituidos por alquilo.
- Se ha demostrado tolerancia a diversos grupos funcionales.
- Aplicabilidad demostrada a los haluros de alquilo primarios, secundarios y terciarios.
- Se ha realizado con éxito la reducción in situ a α-hidroxilsilanos.
Conclusiones:
- Desarrolló un método práctico y eficiente para la síntesis de acilsilano.
- La reacción se lleva a cabo a través de un intermediario de silicio-cobre y un mecanismo de transferencia de electrones.
- Ofrece una ruta versátil para compuestos organosiliconicos funcionalizados.
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