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Una plataforma de acoplamiento reductor promovida por la base para la desfluorización divergente de los

Shawn E Wright¹, Jeffrey S Bandar¹

¹Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States.

Journal of the American Chemical Society

|July 14, 2022

Resumen

Un nuevo método de acoplamiento reductor de trifluorometilareno permite el acceso a diversas subestructuras difluorobencilicas. Esta estrategia de funcionalización de enlaces C-F utiliza una base de Lewis y un reactivo de disilano para una síntesis eficiente de nuevos andamios de difluoroalquileno.

Área de la Ciencia:

Química orgánica
Química del fluor
Metodología sintética

Sus antecedentes:

Los trifluorometilarenos son motivos importantes en los productos farmacéuticos y en los materiales.
Los métodos eficientes para la síntesis de la subestructura difluorobenzílica son limitados.
La funcionalización del enlace C-F ofrece una ruta poderosa hacia nuevas entidades químicas.

Objetivo del estudio:

Desarrollar un nuevo método de acoplamiento reductivo para los trifluorometilarenos.
Ampliar el alcance de las subestructuras difluorobenzílicas accesibles.
Establecer una nueva estrategia de funcionalización de los bonos C-F.

Principales métodos:

El acoplamiento reductor catalizador de Lewis de los trifluorometilarenos.
Uso de reactivos de disilano y formamida como disolvente.
Aislamiento y caracterización de los intermediarios de difluorobenzilo silano.

Principales resultados:

Se estableció un nuevo método de acoplamiento reductor de trifluorometileno.
La reacción sustituye selectivamente un átomo de trifluorometil fluorino.
Se logró el acceso a más de 20 andamios de difluoroalquileno únicos.
Se identificó y aisló un intermediario de difluorobenzilo silano.

Conclusiones:

El método desarrollado amplía significativamente la utilidad sintética de los trifluorometilarenos.
Este enfoque de funcionalización de enlaces C-F proporciona un acceso rápido a los valiosos andamios de difluoroalquileno.
La metodología ofrece una nueva herramienta para construir moléculas orgánicas fluoradas complejas.

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