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La aminofluorización intermolecular catalizada por el paladio de los estirenos

Shuifa Qiu¹, Tao Xu, Juan Zhou

¹State Key Laboratory of Organometallics Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China, 200032.

Journal of the American Chemical Society

|February 13, 2010

Resumen

Una nueva reacción catalizada por el paladio permite la aminofluorización de estirenos utilizando N-fluorobenzenesulfonimida (NFSI) como reactivo dual. Este método produce de manera eficiente productos de fluoroaminas vecinas con alta regioselectividad.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Fluoración Química de la fluoración

Sus antecedentes:

Las reacciones catalizadas por el paladio son vitales en la síntesis orgánica moderna.
El desarrollo de métodos eficientes para la introducción de grupos de flúor y aminas en moléculas orgánicas es un desafío significativo.
Los derivados del estireno son bloques de construcción importantes en varias aplicaciones químicas.

Objetivo del estudio:

Desarrollar una nueva aminofluoración intermolecular catalizada por el paladio de los estirenos.
Para utilizar el N-fluorobenzenesulfonimida (NFSI) como un reactivo de doble fluoración y aminación.
Para lograr una alta regioselectividad en la formación de productos fluoroamínicos vecinos.

Principales métodos:

Empleando un catalizador de paladio con un ligando de nitrógeno secundario.
Utilizando N-fluorobenzenesulfonimida (NFSI) como el único reactivo para la incorporación de flúor y aminas.
Reaccionando con derivados de estireno bajo condiciones catalíticas optimizadas.

Principales resultados:

Desarrollo exitoso de una nueva aminofluoración intermolecular catalizada por el paladio de los estirenos.
Se observó una alta regioselectividad en la formación de productos fluoroamínicos vecinos.
Demostración de la doble función de NFSI como agente fluorinante y aminante.

Conclusiones:

El método desarrollado ofrece una ruta eficiente a las fluoroaminas vecinas.
La fluoropaladación del estireno se propone como un paso clave en el mecanismo de formación de enlaces C-F.
El uso de un ligando de nitrógeno bidental es crítico para el éxito de la reacción.

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