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Fluoración electrofílica de la esfera externa de los complejos organometálicos

Lucy M Milner¹, Natalie E Pridmore¹, Adrian C Whitwood¹

¹Department of Chemistry, University of York , Heslington, York YO10 5DD, United Kingdom.

Journal of the American Chemical Society

|August 14, 2015

Resumen

Los investigadores desarrollaron un nuevo método catalizado por rutenio para crear enlaces carbono-fluoro en la química del organofluoro. Este enfoque fluoriza eficientemente los sustratos no activados, produciendo valiosos enlaces alquenilo y alquilo C-F con alta selectividad.

Área de la Ciencia:

Química del fluoro orgánico
Catálisis
Ciencias de los materiales

Sus antecedentes:

Los compuestos de organofluoro son cruciales en los productos farmacéuticos, los productos agroquímicos y la ciencia de los materiales.
La síntesis de enlaces carbono-fluoro con control sigue siendo un desafío sintético significativo.
Los métodos de fluoración catalizada por metales existentes tienen limitaciones en el alcance del sustrato y la tolerancia del grupo funcional.

Objetivo del estudio:

Desarrollar un nuevo método para la formación de nuevos enlaces alqueno y alquilo carbono-fluoro.
Para lograr una regioquímica controlada y una alta selectividad utilizando sustratos no activados.
Explorar la utilidad de los complejos de rutenio en la fluoración electrofílica de la esfera externa.

Principales métodos:

Utilizó complejos de rutenio para mediar las reacciones de fluoración.
Empleado un mecanismo de fluoración electrofílica de la esfera exterior.
Investigó la reacción con sustratos no activados como la piridina y las alquinas terminales.

Principales resultados:

Se han formado con éxito nuevos enlaces alqueno C ((sp2) -F y alquilo C ((sp3) -F.
Se ha logrado una alta regioselectividad y diastereoselectividad en la formación de enlaces C-F.
Los ligandos fluorados permanecieron coordinados con el centro de rutenio, lo que permitió una mayor reactividad.

Conclusiones:

Se ha informado de un mecanismo de fluoración electrofílica de la esfera exterior sin precedentes utilizando rutenio.
Se ha demostrado la síntesis de valiosas especies organometálicas fluoradas a partir de precursores simples.
El método desarrollado amplía el conjunto de herramientas para la construcción de compuestos orgánicos fluorados complejos.

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