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Arylación catalizada por paladio de las fluoroalquilaminas

Andrew T Brusoe¹, John F Hartwig¹

¹Department of Chemistry, University of California, Berkeley, California 94720, United States.

Journal of the American Chemical Society

|June 13, 2015

Resumen

Este estudio introduce un nuevo método para sintetizar anilinas fluoradas utilizando la catálisis del paladio. Este enfoque supera las limitaciones anteriores, permitiendo la creación de compuestos valiosos con propiedades únicas para diversas aplicaciones.

Área de la Ciencia:

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

Sus antecedentes:

Los derivados de la anilina son cruciales en la química medicinal y la ciencia de los materiales.
Los métodos de síntesis tradicionales para las anilinas sustituidas se enfrentan a desafíos con la estabilidad y la tolerancia del grupo funcional.
Los compuestos orgánicos fluorados ofrecen propiedades físico-químicas únicas.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por paladio para la síntesis de anilinas fluoradas.
Para abordar la inestabilidad de los productos de fluoroalquilanilina bajo condiciones estándar de acoplamiento C-N.
Explorar la utilidad de los grupos fluoroalquilo como sustituyentes distintos de retiro de electrones en las anilines.

Principales métodos:

Acoplamiento catalizado por paladio de fluoroalquilaminas con bromuros de arilo y cloruros de arilo.
Utilizó una base más débil, el fenóxido de potasio (KOPh), rara vez empleado en el acoplamiento cruzado C-N.
Se empleó un sistema catalizador compuesto por AdBippyPhos y [Pd(allyl) Cl]2.

Principales resultados:

Alcanzó altos rendimientos en la síntesis de anilinas fluoradas.
Se ha demostrado la formación exitosa de enlaces C-N en condiciones suaves (baja carga del catalizador <0,50 mol %).
Demostró tolerancia a diversos grupos funcionales incompatibles con bases sólidas.

Conclusiones:

El método desarrollado proporciona un acceso eficiente a valiosas anilinas fluoradas.
El uso de KOPh y el sistema de catalizador específico supera las limitaciones de las reacciones de acoplamiento C-N anteriores.
Las propiedades únicas de los sustituyentes de fluoroalquilo ofrecen nuevas posibilidades en el diseño molecular.

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