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Borilación C-H orto-selectiva catalizada por Rh de arenas N-funcionalizadas con ligandos de monofosfina de cabeza de

Soichiro Kawamorita¹, Tatsuya Miyazaki, Hirohisa Ohmiya

¹Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.

Journal of the American Chemical Society

|November 4, 2011

Resumen

La nueva catálisis de rodio (Rh) permite la boroilación C-H orto-selectiva de arenas con grupos dirigentes de nitrógeno. Este método ofrece una excelente regioselectividad y complementa la catálisis de iridio (Ir) para grupos de dirección basados en oxígeno.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis es la catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

La activación y la funcionalización de C-H son transformaciones clave en la química orgánica moderna.
La borilación C-H orto-selectiva es un método valioso para sintetizar arenes sustituidos.
Los métodos existentes catalizados por iridio son efectivos para los grupos de dirección basados en oxígeno.

Objetivo del estudio:

Desarrollar un nuevo sistema catalítico para la borilación orto-selectiva de C-H utilizando grupos de dirección a base de nitrógeno.
Investigar el alcance y las limitaciones del nuevo sistema catalítico.
Para complementar las metodologías de borilación C-H existentes.

Principales métodos:

Preparación in situ de los sistemas soportados de fosfina y rodio (Rh).
Utilizando monofosfinas de cabeza de puente soportadas por sílice y [Rh (OH) (bacalao) ] (II).
Prueba del sistema catalítico con varias arenas que contienen grupos de dirección a base de nitrógeno.

Principales resultados:

Logró una excelente boroilación orto-selectiva de C-H para una variedad de arenas con grupos N-directivos.
Se ha demostrado una alta regioselectividad con N-heterociclos saturados/insaturados, grupos tert-aminoalquilo y enlaces C-N tipo imina.
Mostró una tolerancia significativa al obstáculo estérico alrededor del enlace C-H.

Conclusiones:

Los sistemas apoyados de fosfina-Rh proporcionan un método eficaz para la borilación orto-selectiva de C-H.
Este enfoque catalizado por Rh amplía el alcance de la borilación C-H para sustratos que contienen N.
El método desarrollado sirve como una valiosa alternativa a la borilación catalizada por Ir.

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