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Carboperfluoroalquilación estereoselectiva Pd catalizada de los alquinos

Zhaodong Li¹, Andrés García-Domínguez¹, Cristina Nevado¹

¹Department of Chemistry, University of Zurich , Winterthurerstrasse 190, CH 8057 Zurich, Switzerland.

Journal of the American Chemical Society

|August 27, 2015

Resumen

Este estudio introduce una reacción catalizada por el paladio para la síntesis de perfluoroalquenos trisubstituidos. El método combina de manera eficiente las alquinas, los ácidos bóricos y los yoduros perfluoroalquilo con un alto control regional y estéreo.

Área de la Ciencia:

Química orgánica
Química organometálica
Química del fluor

Sus antecedentes:

Las reacciones catalizadas por el paladio son cruciales para la formación de enlaces C-C.
Los perfluoroalquenos son bloques de construcción valiosos en la ciencia de los materiales y los productos farmacéuticos.
La síntesis eficiente de fluoroalquenos altamente sustituidos sigue siendo un desafío.

Objetivo del estudio:

Desarrollar una nueva reacción de tres componentes para sintetizar perfluoroalquenos trisubstituidos.
Para lograr una alta regioselectividad y estereoselectividad en la adición de grupos arilo y perfluoroalquilo a través de un enlace triple.

Principales métodos:

Una reacción de tres componentes catalizada por el paladio.
Se utilizan alquinas terminales, ácidos borónicos y yoduros perfluoroalquilo.
Se empleó un proceso mediado por radicales para la adición simultánea de grupos.

Principales resultados:

Se han sintetizado con éxito tres perfluoroalquenos sustituidos.
Se obtiene un alto nivel de control regional y estéreo durante la reacción.
Demostrado amplio alcance de sustrato y tolerancia de grupo funcional.

Conclusiones:

La reacción catalizada por Pd desarrollada ofrece una ruta directa y eficiente a los perfluoroalquenos complejos.
Este método proporciona una herramienta valiosa para acceder a los compuestos orgánicos fluorados.

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