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La difluoración catalítica y diastereoselectiva de 1,2-alquenos

Steven M Banik¹, Jonathan William Medley¹, Eric N Jacobsen¹

¹Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society

|April 6, 2016

Resumen

Este estudio introduce un método catalítico directo para la difluoración de alquenos utilizando fluoruro y un oxidante con un catalizador de yodo de arilo. El proceso produce difluoruros vicinales con alta estereoselectividad, aplicables a varios tipos de alquenos.

Área de la Ciencia:

Química orgánica
Química de la fluoración
Catálisis

Sus antecedentes:

La difluoración de 1,2-alquenos es una transformación crucial en la química sintética.
Los métodos existentes a menudo requieren condiciones duras o carecen de una amplia aplicabilidad.

Objetivo del estudio:

Desarrollar un método directo, catalítico y versátil para la difluoración de alquenos.
Para lograr una alta diastereoselectividad en la formación de difluoruros vicinales.

Principales métodos:

Utilizó una fuente de fluoruro nucleofílico y un oxidante.
Se utiliza un catalizador de yoduro de arilo para la reacción de difluoración directa.
Se ha investigado la aplicabilidad en diversos patrones de sustitución de alquenos.

Principales resultados:

Se ha conseguido la difluoración catalítica directa de varios alquenos.
Los productos se obtuvieron generalmente con altas diastereoselectividades.
Aplicabilidad demostrada a los alquenos con diversos patrones de sustitución.

Conclusiones:

El método desarrollado ofrece una ruta eficiente a los difluoruros vecinos.
Las vías de asistencia anquimérica están implicadas en la estereoinducción para sustratos específicos.
Este enfoque catalítico amplía el conjunto de herramientas sintéticas para las reacciones de fluoración.

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