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B(C₆F₅)₃-Reacción de desproporcionamiento catalizada (convergente) de los indoles

Yuxi Han¹, Sutao Zhang¹, Jianghua He¹

¹State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University , Changchun, Jilin 130012, China.

Journal of the American Chemical Society

|May 9, 2017

Resumen

Un nuevo catalizador de boro libre de metales facilita la desproporcionamiento del indol con los hidrosilanos, logrando altos rendimientos de indolos siliciados con C3. Este proceso eficiente funciona en condiciones suaves y libres de disolventes con una baja carga de catalizador y una excelente reciclabilidad.

Área de la Ciencia:

Química organometálica
Catálisis
Síntesis orgánica

Sus antecedentes:

La funcionalización del indole es crucial en la síntesis orgánica.
El desarrollo de sistemas catalíticos sin metales ofrece alternativas más ecológicas.
Las reacciones de desproporcionamiento eficientes son deseables para la economía atómica.

Objetivo del estudio:

Desarrollar un sistema catalítico sin metales para la desproporcionamiento del indol.
Investigar el mecanismo de reacción y optimizar las condiciones.
Para obtener altos rendimientos de indoles silificados con C3.

Principales métodos:

Utilizado B ((C6F5) 3) como catalizador libre de metales.
Utilizó varios indoles e hidrosilanos.
Se han realizado estudios de RMN in situ para caracterizar los productos intermedios.
Realizó experimentos de control para dilucidar el mecanismo.

Principales resultados:

Se han logrado conversiones casi cuantitativas y hasta un rendimiento del 99% de indoles silificados con C3.
Se ha demostrado un excelente rendimiento catalítico con una carga de catalizador baja (0,01 mol %) en condiciones libres de disolventes.
Demostró una larga actividad catalítica durante 10 adiciones secuenciales.
Propuso un mecanismo de reacción detallado, que permite la supresión de las reacciones secundarias.

Conclusiones:

Se ha desarrollado una desproporción catalizada eficiente de indoles sin metales.
La reacción se lleva a cabo sin aditivos y no produce moléculas pequeñas.
El proceso optimizado es económico y adecuado para aplicaciones prácticas.

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