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Hidrogenación de los fluoroarenos: Acceso directo a todos los cicloalcanos cis-multifluorados

Mario P Wiesenfeldt¹, Zackaria Nairoukh¹, Wei Li¹

¹Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany.

Science (New York, N.Y.)

|August 12, 2017

Resumen

Los investigadores desarrollaron un nuevo método para sintetizar todos los cicloalcanos cis-multifluorados. Este proceso eficiente de un solo paso utiliza la catálisis del rodio-ciclo (alquilo) y el aminocarbeno para preparar materiales valiosos en la ciencia de los materiales.

Área de la Ciencia:

Química orgánica
Ciencias de los materiales
Catálisis

Sus antecedentes:

Los cicloalcanos multifluorados poseen altos momentos dipolo, lo que los hace valiosos en la ciencia de los materiales.
Las rutas sintéticas existentes a menudo son de varios pasos y complejas, lo que limita la accesibilidad.

Objetivo del estudio:

Desarrollar una síntesis escalable en un solo paso para todos los cicloalcanos cis-multifluorados.
Proporcionar acceso a valiosos motivos fluorados para aplicaciones de materiales.

Principales métodos:

Hidrogenación catalizada por el cíclico de rodio (alquilo) y el aminocarbeno (CAAC).
Utilizan arenas fluoradas fácilmente disponibles como precursores.
Reacciones realizadas en disolvente de hexano.

Principales resultados:

Se ha conseguido una preparación escalable en un solo paso de diversos cicloalcanos multifluorados y multisubstituidos.
Se ha sintetizado con éxito todo el cis-1,2,3,4,5,6-hexafluorociclohexano.
Preparados de heterociclos alifáticos fluorados de configuración cis.

Conclusiones:

La hidrogenación catalizada por rhodium-CAAC reportada ofrece una ruta eficiente a los valiosos cicloalcanos todo-cis-multifluorados.
Este método simplifica la síntesis de complejos motivos fluorados.
Permite un uso más amplio de estos compuestos en la ciencia de los materiales.

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