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La activación del enlace carbono-silicio catalizado por el rodio para la síntesis de derivados del benzosilole

Masahiro Onoe¹, Katsuaki Baba, Yoonjoo Kim

¹Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

Journal of the American Chemical Society

|November 7, 2012

Resumen

Una nueva reacción catalizada por el rodio sintetiza eficientemente derivados de benzosiloles mediante el acoplamiento de grupos sililo con alquinos. Este método ofrece una amplia tolerancia de grupo funcional y permite la síntesis modular de materiales avanzados para la electrónica orgánica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química organometálica Química orgánica de los metales.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Los derivados de benzosiloles son importantes andamios en la electrónica orgánica.
Las rutas sintéticas eficientes para los benzosiloles funcionalizados son limitadas.
La activación de los enlaces silicio-carbono generalmente requiere condiciones duras.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento catalizada por rodio para sintetizar benzosiloles 2,3-disubstituidos.
Para explorar la compatibilidad de varios grupos funcionales en la reacción.
Para investigar la síntesis de sistemas π extendidos como los disisilaindacenos y los benzosiloles Si-quiral.

Principales métodos:

Acoplamiento catalizado por el rodio del ácido 2-trimetilsilfenilborónico con alquinas internas.
Exploración del alcance de la reacción y la tolerancia del grupo funcional.
Estudios mecanicistas que involucran efectos sustituyentes.
Demostración de acoplamiento secuencial para la síntesis de moléculas complejas.

Principales resultados:

Síntesis exitosa de diversos benzosiloles 2,3-disubstituidos con amplia compatibilidad de grupo funcional.
Síntesis modular del 1,5-dihidro-1,5-disila-s-indaceno asimétricamente sustituido.
Identificación de un mecanismo de escisión de enlace C-Si mediado por rodio, evitando las especies de silicio hipercoordinadas.
Demostración del potencial para la síntesis asimétrica catalítica de las benzosilolas Si-chiral.

Conclusiones:

Se ha establecido un método versátil catalizado por rodio para la síntesis de benzosiloles.
La reacción procede a través de una vía de activación de enlace C-Si mediada por rodio sin precedentes.
Esta metodología proporciona acceso a bloques de construcción valiosos para la electrónica orgánica y los compuestos de silicio quiral.

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