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Acoplamiento cruzado estereospecífico sin metales de transición con ácidos alquenilborónicos como nucleófilos

Chengxi Li¹, Yuanyuan Zhang¹, Qi Sun¹

¹State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences , 345 Ling Ling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|August 13, 2016

Resumen

Este estudio introduce un nuevo método de acoplamiento cruzado sin metales de transición para crear moléculas complejas. Este nuevo enfoque ofrece una vía estereospecífica para sintetizar valiosos compuestos orgánicos quirales y no quirales.

Área de la Ciencia:

Química orgánica
Metodología sintética
Catálisis

Sus antecedentes:

Las reacciones de acoplamiento cruzado catalizadas por metales de transición son cruciales para la formación de enlaces C-C.
Los métodos existentes a menudo requieren metales de transición caros o tóxicos.
La síntesis estereospecífica de enlaces C ((sp2) -C ((sp3) sigue siendo un desafío importante.

Objetivo del estudio:

Desarrollar una reacción de acoplamiento cruzado sin metales de transición.
Para permitir la síntesis de compuestos no quirales y quirales alquilo-arilo/alqueno.
Para lograr el acoplamiento estereospecífico utilizando ácidos alquenilborónicos.

Principales métodos:

Reacción de acoplamiento cruzado entre haluros de alquilo/mesilados secundarios y ácidos arilo/alquenilborónicos.
Utilizó un sistema de reacción libre de metales de transición.
Mecanismo de acoplamiento estereospecífico tipo SN2 investigado con ácidos alquenilborónicos.

Principales resultados:

Se ha logrado con éxito el acoplamiento cruzado libre de metales de transición.
Sintetizó una gama de productos de acoplamiento quiral y no quiral en rendimientos moderados a buenos.
Demostró el primer acoplamiento estereospecífico de tipo SN2 con ácidos alquenilborónicos como nucleófilos.

Conclusiones:

Se ha establecido una nueva y eficiente metodología de acoplamiento cruzado sin metales de transición.
Este método proporciona una alternativa valiosa a las reacciones catalizadas por metales de transición para la formación de enlaces C ((sp2) -C ((sp3).
El acoplamiento estereospecífico desarrollado ofrece una nueva ruta para sintetizar moléculas quirales.

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