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Arilación en cascada selectiva catalizada por paladio del anión monocarborano de 12 vértices por activación B-H

Furong Lin¹, Jing-Lu Yu¹, Yunjun Shen¹

¹Department of Chemistry , Zhejiang University , 38 Zheda Road , 310027 Hangzhou , People's Republic of China.

Journal of the American Chemical Society

|September 21, 2018

Resumen

Los investigadores desarrollaron un nuevo método para sintetizar carboranos penta-arilados de jaula utilizando catálisis de paladio. Esta reacción de una sola olla funciona de manera eficiente los enlaces inertes, creando nuevos bloques de construcción simétricos de 5 veces.

Área de la Ciencia:

Química organometálica
Química del boro
Metodología sintética

Sus antecedentes:

Los carboranos son grupos de boro versátiles con propiedades electrónicas y estructurales únicas.
La funcionalidad directa de los enlaces B-H de la jaula sigue siendo un desafío sintético.
Las reacciones de acoplamiento cruzado catalizadas por paladio son herramientas poderosas en la síntesis orgánica.

Objetivo del estudio:

Desarrollar un nuevo método catalizado por el paladio para sintetizar carboranos penta-arilados.
Lograr la funcionalización directa de los enlaces B-H utilizando una estrategia de grupo de dirección.
Explorar la síntesis de nuevos bloques de construcción de carborano con aplicaciones potenciales en la ciencia de los materiales y la medicina.

Principales métodos:

Síntesis del anión monocarbocloso-dodecaborato [CB11H12]-.
Acoplamiento intermolecular catalizado por paladio del grupo directivo del ácido C-carboxílico con los iodoarenos.
Funcionalización directa del enlace B-H de la jaula mediante un procedimiento de una sola olla.
Cálculos de la teoría funcional de la densidad (DFT) para aclarar los mecanismos de reacción.

Principales resultados:

Síntesis exitosa de una serie de carboranos penta-arilados en jaula con altos rendimientos.
Demostración de una activación mediada por un grupo dirigido de enlaces inertes B-H.
Se obtiene una alta tolerancia funcional del grupo y una completa regioselectividad de la jaula.
Se propuso un ciclo catalítico Pd (II) -Pd (IV) -Pd (II) que involucra un centro de paladio "caminante".

Conclusiones:

Se ha establecido un método nuevo, eficiente y regioselectivo para sintetizar carboranos penta-arilados.
La metodología desarrollada permite la construcción de arquitecturas complejas de carborano con simetría de 5 veces.
Este trabajo amplía la caja de herramientas sintéticas para la química del carborano y abre caminos para el desarrollo de nuevos materiales.

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