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Arilación catalizada por el cobre de 1H-perfluoroalcanes

Ilya Popov¹, Sergey Lindeman, Olafs Daugulis

¹Department of Chemistry, University of Houston, Houston, Texas 77204-5003, USA.

Journal of the American Chemical Society

|June 2, 2011

Resumen

Los investigadores desarrollaron un nuevo método para arilar los perfluoroalcanes utilizando yoduro de arilo y un catalizador de cobre. Este avance simplifica la síntesis de valiosos compuestos orgánicos fluorados.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química del flúor Química del flúor

Sus antecedentes:

Los perfluoroalcanes son bloques de construcción importantes en los productos farmacéuticos y la ciencia de los materiales.
La funcionalización directa de los enlaces C-H en los perfluoroalcanes sigue siendo un desafío.

Objetivo del estudio:

Desarrollar un método general y eficiente para la arilación de 1H-perfluoroalcanos.
Explorar el alcance y las limitaciones de la reacción de arilación desarrollada.

Principales métodos:

Utilizados reactivos de yoduro de arilo y 1H-perfluoroalcano.
Se emplea 1,3-dimetil-3,4,5,6-tetrahidropirimidina-2(1H) -one (DMPU) como disolvente. también se utiliza en la preparación de bebidas.
Se utiliza el bis ((2,2,6,6-tetrametilpiperidino) zinc (TMP ((2) Zn) como base.
Incorpora un sistema de catalizador de cloruro de cobre y fenantrolina.

Principales resultados:

Se logró con éxito la arilación de 1H-perfluoroalcanos fácilmente disponibles.
Demostró un método general aplicable a varios sustratos de perfluoroalcanos.
Inició investigaciones mecanicistas preliminares para comprender la vía de reacción.

Conclusiones:

El método desarrollado proporciona una nueva ruta para la síntesis de perfluoroalcanos arilados.
Este trabajo amplía la caja de herramientas sintéticas para la química del organofluoruro.
Se necesitan más estudios mecanicistas para aclarar completamente la reacción.

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