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Desoxitrifluorometilación de los alcoholes

Nicholas E Intermaggio¹, Agustin Millet¹, Dali L Davis¹

¹Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|July 5, 2022

Resumen

Los investigadores desarrollaron un nuevo método para la desoxitrifluorometilación de los alcoholes. Esta reacción catalizada por el cobre permite la formación directa de enlaces C ((sp3) - CF3, ofreciendo una herramienta valiosa para la química medicinal.

Área de la Ciencia:

Química orgánica
Química medicinal
Catálisis

Sus antecedentes:

La desoxigenación de los alcoholes es crucial en la medicina moderna.
La desoxifluoración introduce átomos de flúor en las moléculas del fármaco.
El grupo trifluorometilo (CF3) mejora las propiedades farmacológicas, pero su incorporación a través de la trifluorometilación desoxigenativa de alcoholes es un desafío.

Objetivo del estudio:

Desarrollar un método general para la desoxigenación trifluorometilación directa de los alcoholes.
Para permitir la incorporación del grupo trifluorometilo en moléculas derivadas del alcohol.

Principales métodos:

Catalización por fotorredóxido de cobre.
Activación in situ de sustratos alcohólicos con sales de benzoxazolio.
Formación de bonos C ((sp3) - CF3.

Principales resultados:

Se logró una nueva desoxitrifluorometilación directa de alcoholes catalizada por el cobre.
El método facilita la formación de enlaces C ((sp3) - CF3 a partir de los precursores del alcohol.
Se utilizaron sales de benzoxazolio para la activación in situ del sustrato.

Conclusiones:

Este estudio informa un avance significativo en las reacciones de desoxitrifluorometilación.
El método desarrollado proporciona una ruta general para incorporar el valioso grupo CF3 en moléculas.
Esto ofrece una nueva estrategia para el descubrimiento y desarrollo de fármacos.

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