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Síntesis de éter de diarilo mediada por bis ((triarilmetilo): arilación oxidativa de fenoles con

Terunobu Saitoh¹, Junji Ichikawa

¹Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Journal of the American Chemical Society

|July 7, 2005

Resumen

Un nuevo método sintetiza éteres de arilo dialquilaminofenilo de manera eficiente sin calentar. Esta arilación oxidativa utiliza un nuevo catalizador de dication para la sustitución basada en radicales, ofreciendo una ruta sintética más ecológica.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química sintética de la química sintética.

Sus antecedentes:

Los éteres de arilo son importantes motivos estructurales en los productos farmacéuticos y en la ciencia de los materiales.
La síntesis eficiente de éteres de arilo sustituidos sigue siendo un desafío clave en la química orgánica.

Objetivo del estudio:

Desarrollar un método novedoso, eficiente y suave para la síntesis de varios éteres de arilo 4-dialquilaminofenilo.
Para explorar el mecanismo de la arilación oxidativa utilizando un catalizador de dication específico.

Principales métodos:

Reacción de los fenoles con las N,N-dialquil-4-feniltioanilinas.
La catálisis por una dicción bis ((diphenylmethylium) naphthalenediyl.
Proceso radical que implica la ipso-sustitución del grupo feniltio.

Principales resultados:

Varios éteres de arilo 4-dialquilaminofenilo fueron sintetizados con buen rendimiento.
La reacción procedió de manera eficiente sin necesidad de calentamiento.
El sistema catalítico demostró una promoción efectiva de la arilación oxidativa.

Conclusiones:

Se ha establecido un método novedoso y eficiente para la síntesis de éter de arilo.
La dication bis ((diphenylmethylium) naphthalenediyl es un catalizador eficaz para esta transformación.
La reacción se produce a través de un mecanismo radical que incluye la ipso-sustitución.

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