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Dearomativo [2 + 2] Cicloadición y reacción formal de inserción C-H de o-carborina con indoles: síntesis de

Da Zhao¹, Jiji Zhang¹, Zuowei Xie¹

¹Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.

Journal of the American Chemical Society

|July 11, 2015

Resumen

La o-carborina permite una síntesis eficiente de los heterociclos funcionalizados con carborano. Este estudio detalla las reacciones con indoles protegidos por N, que producen indolinas fusionadas o indoles de carboranilo a través de nuevas vías de cicloadición o inserción de C-H.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química organometálica Química orgánica de los metales.
Química Heterocíclica La Química Heterocíclica es una de las más conocidas.

Sus antecedentes:

o-Carboryne es un sintón versátil para los heterociclos funcionalizados con carborano.
Los indoles son importantes compuestos heterocíclicos con diversas aplicaciones.

Objetivo del estudio:

Para explorar la reactividad de la o-carborina con los indoles protegidos por N.
Desarrollar métodos sintéticos eficientes para indolos y indolinas funcionalizados con carborano.
Para investigar el mecanismo de las reacciones de cicloadición y inserción de C-H observadas.

Principales métodos:

Reacción de la o-carborina con varios indoles protegidos por N.
Caracterización de productos utilizando la espectroscopia de RMN (1H, 13C, 11B) y el MSRH.
Análisis de rayos X monocristalino para la confirmación estructural.

Principales resultados:

Dearomativa [2 + 2] cicloadición con indoles protegidos por TMS dando indolinas fusionadas con carborano.
La inserción formal de C-H con indoles N-alquilo produce indoles de carboranilo.
Se observó una doble reactividad con los indoles de N-arilo, con relaciones de producto influenciadas por los sustituyentes de anillos de arilo.
Se ha demostrado la compatibilidad con otros heteroaromáticos.
La primera adición de ciclo aromática [2 + 2] libre de metales y rayos UV de indoles fue reportada por primera vez.

Conclusiones:

Desarrolló protocolos generales y eficientes para sintetizar indolos, indolinas y otros heterociclos funcionalizados con carborano.
Estableció un mecanismo de reacción paso a paso que explica los resultados observados.
Destacó la importancia de la o-carborina como un elemento clave en la síntesis orgánica.

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