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Alcoxiboración: adición de cierre de anillo de enlaces B-O σ a través de alquinas
Joshua J Hirner1, Darius J Faizi, Suzanne A Blum
1Department of Chemistry, University of California, Irvine , Irvine, California 92617-2025, United States.
Journal of the American Chemical Society
|March 5, 2014
Resumen
Los investigadores desarrollaron una nueva reacción de alkoxiboración, que permite la adición de enlaces boro-oxígeno a los alquinos. Este avance proporciona acceso directo a valiosos compuestos orgánicos orgánicos que contienen oxígeno para la síntesis.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química organometálica Química orgánica de los metales.
Sus antecedentes:
- Los reactivos de organoboron generalmente se sintetizan a través de la adición de enlaces sigma de boro-X a los enlaces múltiples carbono-carbono.
- El fuerte enlace boro-oxígeno ha impedido históricamente su activación directa para las reacciones de adición, limitando el acceso a los compuestos de organoboro que contienen oxígeno.
Objetivo del estudio:
- Desarrollar una nueva reacción de alkoxiboración para la adición directa de enlaces sigma de boro-oxígeno a los alquinos.
- Establecer un método suave y tolerante a los grupos funcionales para la síntesis de reactivos organoborónicos que contienen oxígeno.
Principales métodos:
- Utilizó una estrategia de catálisis de oro para activar el enlace sigma boro-oxígeno.
- Investigó la adición de enlaces sigma de boro-oxígeno a varios alquinos.
Principales resultados:
- Realizó con éxito la reacción de alkoxiboración, logrando la adición de enlaces sigma de boro-oxígeno a los alquinos.
- Produjo derivados funcionalizados de ácido borónico O-heterocíclico.
- Compatibilidad demostrada de amplio grupo funcional y condiciones de reacción leve.
Conclusiones:
- La alcosiboración catalizada por oro desarrollada ofrece una ruta nueva y directa a los reactivos organoboron que contienen oxígeno.
- Este método supera las limitaciones anteriores asociadas con la activación de enlaces boro-oxígeno.
- Los compuestos sintetizados tienen potencial para aplicaciones de síntesis divergentes.
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