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Acoplamiento directo C-N de los imidazoles con compuestos aromáticos y bencílicos a través de la funcionalización

Tatsuya Morofuji¹, Akihiro Shimizu, Jun-ichi Yoshida

¹Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University , Nishikyo-ku, Kyoto 615-8510, Japan.

Journal of the American Chemical Society

|March 15, 2014

Resumen

Un nuevo método electrooxidativo de funcionalización C-H permite un acoplamiento C-N eficiente de los imidazoles. Este enfoque evita la sobreoxidación mediante la formación de iones de imidazolio protegidos, dando lugar a diversos imidazoles sustituidos por N.

Área de la Ciencia:

Química orgánica es la química orgánica.
La electroquímica es electroquímica.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Los derivados del imidazol son cruciales en los productos farmacéuticos y en la ciencia de los materiales.
La síntesis eficiente de los imidazoles sustituidos por N sigue siendo un desafío.
La funcionalización C-H ofrece una ruta directa a las moléculas complejas.

Objetivo del estudio:

Desarrollar un nuevo método electrooxidativo para el acoplamiento C-N de los imidazoles.
Para lograr la funcionalización regioselectiva C-H de compuestos aromáticos y bencílicos con los imidazoles.
Para sintetizar imidazoles sustituidos por N compatibles con varios grupos funcionales.

Principales métodos:

Funcionalización electrooxidativa C-H de sustratos aromáticos y bencílicos.
Formación y posterior desprotección de iones intermedios de imidazolio.
Utilizando iones de imidazolio protegidos para evitar la sobreoxidación.

Principales resultados:

Acoplamiento exitoso C-N de los imidazoles a través de la electrooxidación.
Compatibilidad demostrada con una amplia gama de grupos funcionales.
Síntesis de un inhibidor de P450 17 y un agente antifúngico con núcleos de imidazol sustituidos por N.

Conclusiones:

El método desarrollado proporciona una ruta fácil y eficiente a los imidazoles N-sustituidos.
Este enfoque electrooxidativo ofrece ventajas en términos de selectividad y tolerancia al grupo funcional.
La metodología es aplicable a la síntesis de compuestos biológicamente relevantes que contienen imidazol.

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