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Arylación directa por C6 catalizada por Cu de los indoles

Youqing Yang¹, Ruirui Li², Yue Zhao¹

¹State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210093, China.

Journal of the American Chemical Society

|July 1, 2016

Resumen

Los investigadores lograron la primera arilación directa y selectiva del sitio de los indolos en la posición C6 utilizando un nuevo grupo de dirección y catálisis de cobre. Este método suave y escalable amplía las posibilidades sintéticas para la funcionalización del indol.

Área de la Ciencia:

Química orgánica
Metodología sintética
Química Heterocíclica

Sus antecedentes:

La arilación directa ofrece una ruta eficiente para la formación de enlaces C-C.
La funcionalización regioselectiva de los indolos, particularmente en la posición C6, sigue siendo un desafío.
Los métodos existentes a menudo requieren condiciones duras o carecen de selectividad del sitio.

Objetivo del estudio:

Desarrollar el primer protocolo de arilación directa y selectiva del sitio para los indolos en la posición C6.
Establecer un método suave y eficiente aplicable a una amplia gama de sustratos.
Para demostrar la escalabilidad del protocolo desarrollado.

Principales métodos:

Se utilizó un grupo de dirección N-P (O) (t) Bu2 para mejorar la regioselectividad.
Se utilizan sales de trilato de diariliodonio como reactivos de arilación.
Se llevó a cabo la reacción utilizando cantidades catalíticas de óxido de cobre (CuO) en condiciones suaves, sin ligandos o aditivos adicionales.

Principales resultados:

Se ha conseguido con éxito la arilación directa de los indolos exclusivamente en la posición C6.
Se ha demostrado una gran selectividad regional en una amplia gama de socios de acoplamiento de indoles y arenos.
El protocolo demostró ser eficiente, escalable y tolerante con varios grupos funcionales.

Conclusiones:

Este estudio presenta un avance significativo en la arilación directa regioselectiva de los indolos.
El método desarrollado ofrece un enfoque suave, eficiente y escalable para los indoles arilados con C6.
Los hallazgos abren nuevas vías para sintetizar derivados complejos de indol.

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