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Síntesis de dibenzofuranos a través de la activación C-H dirigida por el fenol catalizado por el paladio/ciclización

Bin Xiao¹, Tian-Jun Gong, Zhao-Jing Liu

¹Department of Chemistry, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, China.

Journal of the American Chemical Society

|May 26, 2011

Resumen

Una nueva reacción catalizada por paladio permite una síntesis eficiente de dibenzofuranos a través de la activación de C-H y la ciclización de C-O. El estudio identifica la eliminación reductora de C-O como el paso que limita la tasa, ofreciendo una ruta sintética complementaria.

Área de la Ciencia:

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

Sus antecedentes:

Los dibenzofuranos son importantes compuestos heterocíclicos con diversas aplicaciones.
Los métodos sintéticos existentes para los dibenzofuranos a menudo requieren condiciones duras o grupos de dirección específicos.

Objetivo del estudio:

Desarrollar un método práctico y eficiente para sintetizar dibenzofuranos sustituidos.
Para utilizar la activación de C-H dirigida por fenol y la ciclización de C-O catalizada por el paladio.
Para investigar el mecanismo de reacción, incluido el paso que limita el volumen de negocios.

Principales métodos:

Se empleó un sistema de reacción catalizado por paladio ((0) / paladio ((II)).
La reacción utilizó el aire como un oxidante sostenible.
Los derivados del fenol fueron sometidos a la activación C-H seguida de la ciclización C-O.

Principales resultados:

Se estableció una ruta sintética práctica para los dibenzofuranos sustituidos.
La reacción demostró tolerancia a una amplia gama de grupos funcionales.
La eliminación reductiva de C-O fue identificada como el paso que limita el volumen de negocios, distinto de la activación de C-H.

Conclusiones:

La metodología desarrollada proporciona un enfoque complementario a la síntesis de dibenzofurano existente.
La reacción ofrece una vía práctica y eficiente para acceder a dibenzofuranos funcionalizados.
Comprender el paso limitador de velocidad ayuda a optimizar aún más las reacciones de funcionalización C-H catalizadas por paladio.

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