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Desoxifluoración de alcoholes de 1°, 2° y 3° por activación no básica de O-H y desplazamiento de fluoruro catalizado

Hye Won Moon¹, Marissa N Lavagnino¹, Soohyun Lim¹

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States.

Journal of the American Chemical Society

|October 9, 2023

Resumen

Un nuevo método de desoxifluoración activa los alcoholes utilizando triamida de fósforo y un catalizador de boro. Este proceso permite la estereoinversión para la preparación de alquilfluoruros quirales a partir de alcoholes.

Área de la Ciencia:

Química orgánica
Química de la fluoración

Sus antecedentes:

La desoxifluoración es crucial para la síntesis de compuestos organofluorados.
Los métodos existentes a menudo requieren condiciones duras o tienen un alcance de sustrato limitado.

Objetivo del estudio:

Desarrollar un nuevo método sin bases para la desoxifluoración de varios alcoholes.
Para permitir la síntesis estereoselectiva de los alquilfluoruros quirales.

Principales métodos:

Utilizó una triamida de fósforo no trigonal para la activación del alcohol.
Se utilizó un donante de fluoruro orgánico soluble y un catalizador de triarilborano.
Mecanismos de reacción investigados mediante experimentos mecanicistas.

Principales resultados:

Se ha logrado con éxito la desoxifluoración de alcoholes primarios, secundarios y terciarios.
Se ha demostrado la preparación de alquilfluoruros homoquirales secundarios y terciarios a través de la estereoinversión.
Elucidado un mecanismo que involucra el colapso del par de iones de fluoroborato de oxyphosphonium.

Conclusiones:

El método descrito ofrece un enfoque complementario a las técnicas de desoxifluoración existentes.
Proporciona una herramienta valiosa para acceder a compuestos quirales de organofluoro con estereoquímica controlada.

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