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Reacciones de acoplamiento catalizadas por paladio de tetrafluoroetileno con compuestos de arilzinco

Masato Ohashi¹, Tadashi Kambara, Tsubasa Hatanaka

¹Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Journal of the American Chemical Society

|February 17, 2011

Resumen

Este estudio introduce una nueva reacción de acoplamiento catalizada por el paladio para el tetrafluoroetileno (TFE), que permite la síntesis de derivados del trifluorostireno. Este avance desbloquea nuevas transformaciones catalíticas para los compuestos de organofluoro.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química organometálica Química orgánica de los metales.
Química del flúor Química del flúor

Sus antecedentes:

Los compuestos organofluorados son vitales en la industria química.
El tetrafluoroetileno (TFE) es una materia prima económica, pero tiene aplicaciones limitadas más allá de los polímeros.
La activación catalítica de enlaces C-F de TFE sigue siendo un área poco explorada.

Objetivo del estudio:

Informar sobre la primera transformación catalítica del tetrafluoroetileno (TFE) que involucra la activación del enlace carbono-fluoro.
Desarrollar una nueva reacción de acoplamiento catalizada por paladio utilizando TFE.
Para sintetizar valiosos derivados del α,β,β-trifluorostireno.

Principales métodos:

Reacción de acoplamiento catalizada por paladio.
Utilizado el tetrafluoroetileno (TFE) como sustrato.
Se emplean reactivos de arilzinco y yoduro de litio como aditivos.

Principales resultados:

Logró la primera reacción de acoplamiento catalítico reportada de TFE.
Se ha activado con éxito el enlace carbono-fluoruro en TFE.
Derivados de α,β,β-trifluorostireno sintetizados en excelentes rendimientos.

Conclusiones:

Demostró una nueva ruta sintética para los compuestos organofluorados.
Amplió la utilidad del tetrafluoroetileno (TFE) en la catálisis.
Avenidas abiertas para la nueva síntesis de moléculas fluoradas.

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