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Fluoración descarboxilativa catalizada por plata de los ácidos carboxílicos alifáticos en una solución acuosa

Feng Yin¹, Zhentao Wang, Zhaodong Li

¹Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, PR China.

Journal of the American Chemical Society

|June 15, 2012

Resumen

Este estudio introduce un nuevo método para crear compuestos fluorados. Utiliza nitrato de plata para catalizar la fluoración de los ácidos carboxílicos, produciendo fluoruros de alquilo de manera eficiente bajo condiciones suaves.

Área de la Ciencia:

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

Sus antecedentes:

Los compuestos fluorados son vitales en varias industrias.
La formación de enlaces carbono-fluoro, especialmente en sitios específicos, sigue siendo difícil.

Objetivo del estudio:

Desarrollar un método eficiente y práctico para sintetizar fluoruros de alquilo.
Explorar un nuevo enfoque catalítico para la formación de enlaces C(sp(3)) -F.

Principales métodos:

Utilizando el nitrato de plata (AgNO(3)) como catalizador.
Utilizando SELECTFLUOR® como el reactivo fluorescente.
Llevar a cabo la reacción en solución acuosa bajo condiciones suaves.

Principales resultados:

Logró una fluoración descarboxilativa eficiente de varios ácidos carboxílicos alifáticos.
Sintetizó los correspondientes fluoruros de alquilo en rendimientos satisfactorios.
Demostró la generalidad del método, la quimioselectividad y la compatibilidad entre grupos funcionales.

Conclusiones:

El método de fluoración radical desarrollado es muy práctico para sintetizar moléculas fluoradas.
Un mecanismo propuesto implica la transferencia de un solo electrón mediada por Ag (III) y la transferencia de átomos de flúor.
Esta fluorodecarboxilación catalítica ofrece una herramienta valiosa para la síntesis orgánica.

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