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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
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Acoplamiento cruzado conjuntivo catalítico habilitado por reordenamiento inducido por metales
Liang Zhang1, Gabriel J Lovinger1, Emma K Edelstein1
1Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA.
Science (New York, N.Y.)
|January 2, 2016
Resumen
Los investigadores desarrollaron una nueva reacción catalizada por el paladio que evita la transmitación tradicional. Este nuevo reordenamiento de metales acopla eficientemente organolitios y organoboronatos con organotriflatos, creando ésteres organoboronicos quirales.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- La catálisis de metales de transición es fundamental para la síntesis orgánica moderna.
- Muchos ciclos catalíticos incluyen pasos de transmitación organometálicos, como los del acoplamiento Suzuki-Miyaura.
- Existe la necesidad de vías de reacción alternativas para expandir las capacidades sintéticas.
Objetivo del estudio:
- Introducir una nueva alternativa al paso de transmisión organometálica en las reacciones catalizadas por metales.
- Para demostrar un nuevo mecanismo de reordenamiento inducido por el paladio.
- Desarrollar una nueva reacción de acoplamiento cruzado para sintetizar ésteres organobóricos quirales.
Principales métodos:
- Preparación de complejos de éster vinílico borónico a partir de organoboronatos y reactivos de organolitio.
- Utilizando la catálisis de paladio para inducir una reorganización de la migración 1,2.
- El uso de catalizadores quirales de paladio para la síntesis enantioselectiva.
Principales resultados:
- Los complejos de éster borónico de vinilo se someten a una reorganización inducida por el paladio.
- El reordenamiento implica una migración de 1,2 de los grupos alquilo o arilo del boro al vinilo α-carbono.
- Este proceso forma un enlace C-Pd σ, lo que permite una nueva reacción de acoplamiento cruzado.
- Los ésteres organobóricos quirales fueron sintetizados con alta enantioselectividad a partir de tres materiales de partida simples.
Conclusiones:
- Se ha establecido una nueva reacción elemental, el reordenamiento del metalato inducido por el paladio.
- Esta reacción ofrece una alternativa a la transmitación tradicional en el acoplamiento cruzado.
- El método desarrollado proporciona un acceso eficiente a los ésteres organobóricos enriquecidos enantioméricamente.
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