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Arilboración de alquenos por catálisis cooperativa de paladio y cobre

Kazuhiko Semba¹, Yoshiaki Nakao

¹Department of Material Chemistry, Graduate School of Engineering, Kyoto University , Kyoto 615-8510, Japan.

Journal of the American Chemical Society

|May 10, 2014

Resumen

Una nueva reacción catalizada por paladio/cobre permite la síntesis regioselectiva de compuestos borilados a partir de vinilarenos y haluros de arilo. Este método eficiente es escalable y útil para sintetizar moléculas biológicamente activas como CDP840.

Área de la Ciencia:

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

Sus antecedentes:

Las reacciones de arilboración son cruciales para la formación de enlaces C-C.
El desarrollo de métodos eficientes y regioselectivos para la síntesis de compuestos de organoboron sigue siendo un área activa de investigación.

Objetivo del estudio:

Desarrollar una arilboración de vinillarenos y crotonato de metilo catalizado por el paladio y el cobre.
Para lograr la síntesis regioselectiva de valiosos compuestos orgánicos borilados.

Principales métodos:

Catálisis cooperativa que utiliza complejos de paladio (Pd) y cobre (Cu).
Reacción de los vinilarenos y el crotonato de metilo con haluros de arilo y el bis ((pinacolato) diboron.

Principales resultados:

Síntesis regioselectiva de 2-borilo-1,1-diariletanos y ésteres α-arilo-β-borilo.
La reacción demostró compatibilidad con diversos grupos funcionales.
Escalado con éxito a cantidades de gramos sin comprometer el rendimiento.

Conclusiones:

El sistema catalítico Pd/Cu desarrollado proporciona una ruta eficiente a los compuestos organoboron funcionalizados.
La metodología es robusta, escalable y aplicable a la síntesis de moléculas complejas, incluido el fármaco candidato CDP840.0.

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