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Síntesis catalizada por el cobalto (III) de indazoles y furanos por cascadas de funcionalización/adición/ciclización

Joshua R Hummel¹, Jonathan A Ellman

¹Department of Chemistry, Yale University , New Haven, Connecticut 06520, United States.

Journal of the American Chemical Society

|December 11, 2014

Resumen

Un nuevo catalizador de cobalto permite una síntesis eficiente en un solo paso de N-aril-2H-indazoles y furanos. Este método rentable utiliza materiales de partida simples y es escalable para aplicaciones más amplias en la síntesis química.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Química Heterocíclica La Química Heterocíclica es una de las más conocidas.

Sus antecedentes:

El desarrollo de rutas sintéticas eficientes y rentables para los heterociclos es crucial para la investigación farmacéutica, agroquímica y de materiales.
Los métodos existentes a menudo requieren procedimientos complejos o catalizadores costosos.

Objetivo del estudio:

Desarrollar un nuevo catalizador de cobalto catiónico estable en el aire para la síntesis de N-aril-2H-indazoles y furanos.
Establecer un procedimiento convergente de una sola etapa para el ensamblaje de heterociclos a través de la funcionalización de enlaces C-H.

Principales métodos:

Utilizó un nuevo catalizador catiónico Co(III) estable en el aire para las adiciones de enlaces C-H a los aldehídos.
Utilizó una cantidad subtoiquiométrica de ácido acético (AcOH) como aditivo.
Se ha demostrado la ciclización y la aromatización in situ para la formación de productos.

Principales resultados:

Con éxito sintetizó N-aril-2H-indazoles y furanos en un solo paso.
Las reacciones procedieron eficientemente con varios sustratos aromáticos, heteroaromáticos y alifáticos.
Escalabilidad demostrada hasta 20 mmol, lo que indica potencial para aplicaciones a mayor escala.
Se mostraron nuevas aplicaciones de grupos de dirección en la funcionalización C-H catalizada por Co (III).
Logró la primera funcionalización catalizada por Co (III) de enlaces alquenilo C-H para la síntesis de furanos.

Conclusiones:

El catalizador Co ((III) desarrollado proporciona un método sencillo, rentable y escalable para la síntesis de heterociclos.
Este enfoque amplía la utilidad de la catálisis de Co (III) en la funcionalización de C-H, particularmente para los aldehídos y los enlaces de C-H alquenilo.
La metodología ofrece una herramienta valiosa para acceder a importantes andamios heterocíclicos en química medicinal y de materiales.

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