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Múltiples modos de reactividad dirigidos por enonas conducen a la fluoración fotoquímica selectiva de derivados

Cody Ross Pitts¹, Desta Doro Bume¹, Stefan Andrew Harry¹

¹Department of Chemistry, Johns Hopkins University , 3400 N. Charles Street, Baltimore, Maryland 21218, United States.

Journal of the American Chemical Society

|February 2, 2017

Resumen

Los investigadores desarrollaron un nuevo método fotoquímico para la fluoración selectiva del sitio de moléculas complejas utilizando el grupo funcional de enona. Este avance permite la incorporación precisa de flúor, crucial para el descubrimiento y desarrollo de fármacos.

Área de la Ciencia:

Química orgánica
La fotoquímica
Química medicinal

Sus antecedentes:

La reactividad de la fluoración alifática está bien establecida.
La fluoración selectiva del sitio en moléculas complejas sigue siendo un desafío significativo.
La incorporación de fluor es vital en el descubrimiento de fármacos.

Objetivo del estudio:

Desarrollar un método de fluoración fotoquímica selectiva para moléculas complejas.
Para utilizar el grupo funcional enone para dirigir la fluoración.
Explorar la previsibilidad y el alcance del método desarrollado.

Principales métodos:

Fotoexcitación de algunos grupos funcionales.
Fluoración selectiva del enlace C-H en esteroides y policíclos.
Modelado teórico para predecir los modos de fluoración (gamma, beta, homoalílico y alílico).

Principales resultados:

Se logra una fluoración fotoquímica selectiva del sitio basada en la orientación del oxígeno enónimo.
La fluoración se produjo en hasta 65 enlaces C-H sp3 diferentes en sustratos complejos.
Se ha demostrado una fluoración gamma, beta, homoalílica y alílica predecible.

Conclusiones:

La fotoexcitación de Enone ofrece una solución poderosa para la fluoración selectiva del sitio.
El método avanza en el diseño de estrategias de fluoración selectiva.
Los resultados tienen implicaciones significativas para el descubrimiento de medicamentos que contienen flúor.

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