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Hidroarilación remota terminal catalizada por el rodio de las olefinas activadas a través de una isomerización
Arun Jyoti Borah1, Zhuangzhi Shi1
1State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering , Nanjing University , Nanjing 210093 , China.
Journal of the American Chemical Society
|May 5, 2018
Resumen
La hidroarilación catalizada por Rh permite la alquilación remota de C-H de los indolos y compuestos relacionados. Este método supera las reglas del aceptador de Michael y controla la regioselectividad, avanzando en la isomerización de alceno y la funcionalización C-H.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- Los métodos tradicionales de alquilación C-H a menudo carecen de regioselectividad.
- La adición conjugada a los aceptores de Michael es una vía de reacción común pero a veces limitante.
- Las estrategias de grupo dirigidas son cruciales para lograr la funcionalización específica del sitio en moléculas complejas.
Objetivo del estudio:
- Desarrollar un nuevo método catalizado por Rh para la hidroarilación remota de C-H.
- Para lograr la funcionalización selectiva en la posición C7 de las indolinas y las ortoposiciones de las indolinas/anilinas.
- Para superar las limitaciones asociadas con los aceptores de Michael y la regioselectividad.
Principales métodos:
- Utilizando un catalizador de rodio (Rh).
- Empleando un grupo directivo específico de N-P.
- Aprovechando la isomerización deconjugativa de largo alcance para la activación remota.
Principales resultados:
- Se ha logrado la hidroarilación remota catalizada por Rh en la posición C7 de los indolos.
- Se ha logrado la hidroariación orto-selectiva de las indolinas y anilinas.
- Se ha demostrado la superación de la regla conjugada de los aceptadores de Michael.
- Selectividad posicional controlada en la funcionalización del indol.
Conclusiones:
- Este trabajo presenta un avance significativo en la isomerización de alquenos y la alquilación C-H de los indolos.
- La metodología desarrollada ofrece una herramienta poderosa para la funcionalización regioselectiva de los heterociclos N.
- La estrategia ofrece nuevas posibilidades para sintetizar moléculas orgánicas complejas.
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