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Aryne 1,2,3-Trifuncionalización con sulfóxidos de alilo de arilo

Yuanyuan Li¹, Dachuan Qiu¹, Rongrong Gu¹

¹School of Chemistry and Chemical Engineering, Chongqing University , 174 Shazheng Street, Chongqing 400030, P. R. China.

Journal of the American Chemical Society

|August 17, 2016

Resumen

Este estudio introduce un nuevo método para la trisubstitución de ario utilizando sulfóxidos de arilo-alilo, creando enlaces adyacentes de C-S, C-O y C-C en un anillo de benceno en condiciones suaves.

Área de la Ciencia:

Química orgánica
Metodología sintética
Química del arilo

Sus antecedentes:

La química de aryne ofrece vías únicas para la síntesis de moléculas complejas.
El desarrollo de métodos eficientes para la funcionalización regioselectiva de los anillos aromáticos es crucial.

Objetivo del estudio:

Para lograr la sustitución de 1,2,3-trisubstitución de las arinas por sulfóxidos de arilo-alilo.
Establecer una nueva ruta sintética para incorporar enlaces C-S, C-O y C-C adyacentes en un anillo de benceno.

Principales métodos:

Reacción de las arinas con los sulfóxidos de arilo-alilo.
Condiciones de reacción leves.
Investigaciones mecanicistas preliminares.

Principales resultados:

Se ha conseguido la sustitución de 1,2,3 arinas.
Se ha demostrado la formación de enlaces C-S, C-O y C-C adyacentes.
Se ha observado un amplio alcance de sustrato.

Conclusiones:

Se ha desarrollado un método novedoso y eficiente para la funcionalización de aryne.
La reacción procede a través de un mecanismo en cascada que involucra la cicloadición formal [2+2], la migración S→O y el reordenamiento de Claisen.
Esta metodología proporciona una plataforma versátil para la construcción de compuestos aromáticos altamente sustituidos.

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