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Hidrotrifluoroacetilación de alquenos mediante reactivos enmascarados de diseño

Sangil Han¹, Kyra L Samony¹, Rifat N Nabi¹

¹Department of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania 19122, United States.

Journal of the American Chemical Society

|May 16, 2023

Resumen

Los investigadores desarrollaron un nuevo método de trifluoroacetilación utilizando un reactivo umpolung para convertir los radicales electrófilos en nucleófilos. Este nuevo enfoque permite una eficiente funcionalización en etapa tardía de moléculas complejas y diversos análogos fluorados.

Área de la Ciencia:

Química orgánica
Química medicinal
Química del fluor

Sus antecedentes:

La introducción del grupo trifluorometilacilo (CF3CO) mejora la actividad farmacéutica.
Los métodos existentes para la síntesis de trifluoreketona son limitados.
La química de los radicales trifluoroacetil es en gran parte inexplorada.

Objetivo del estudio:

Desarrollar un nuevo método de trifluoroacetilación.
Para permitir la transformación de radicales electrófilos en radicales nucleófilos.
Para demostrar la utilidad en la última etapa de la funcionalidad de moléculas complejas.

Principales métodos:

Utilizó un reactivo umpolungado para la transformación radical.
Se aplicó el método a la fase tardía de la trifluoracetilación.
Realizó reacciones a gran escala con esclareolida y loratadina.

Principales resultados:

Se logró con éxito la trifluoroacetilación a través de una vía de radicales nucleófilos.
Se ha demostrado una amplia aplicabilidad en moléculas bioactivas complejas.
Mostró la síntesis de varios análogos fluorados de las trifluorometilcetonas.

Conclusiones:

La estrategia de umpolung desarrollada proporciona una nueva vía para la trifluoracetilación.
El método es eficaz para la funcionalización tardía de los productos farmacéuticos.
Ofrece potencial para la síntesis de diversos compuestos fluorados.

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