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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 21, 2014
Arilaciones altamente regioselectivas, secuenciales y múltiples catalizadas por paladio de éteres vinílicos que
P Nilsson1, M Larhed, A Hallberg
1Department of Organic Pharmaceutical Chemistry, Uppsala Biomedical Center, Uppsala University, P.O. Box 574, SE-751 23 Uppsala, Sweden.
Journal of the American Chemical Society
|August 23, 2001
Resumen
Los investigadores desarrollaron nuevas multiarilaciones de Heck aceleradas auxiliares utilizando un grupo dimetilamino coordinador de paladio. Esto permite reacciones de tri- y diarilación eficientes, incluyendo la primera triarilación de Heck y diarilaciones selectivas de éteres de vinilo.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis es la catálisis.
- Metodología sintética de la metodología sintética.
Sus antecedentes:
- Las reacciones de choque son cruciales para la formación de enlaces C-C.
- Desarrollar métodos de multiarrelación eficientes y selectivos sigue siendo un desafío.
- La catálisis guiada por auxiliares ofrece una vía para controlar la reactividad y la selectividad.
Objetivo del estudio:
- Desarrollar nuevas reacciones de multiarilación de Heck aceleradas auxiliarmente.
- Introducir un grupo dimetilamino coordinador de paladio para el control de la quelación.
- Establecer métodos eficientes para la tri- y diarilación de éteres de vinilo.
Principales métodos:
- Presentación intramolecular del complejo de adición oxidativa.
- Utilizando un grupo dimetilamino coordinador de paladio para la aceleración y el control de la quelación.
- Hidrólisis asistida por microondas para la eliminación del grupo de dirección del catalizador.
Principales resultados:
- Informó el primer ejemplo de un proceso de triarilación de Heck.
- Se lograron diarilaciones altamente selectivas catalizadas por paladio de éteres de alquilo vinilo.
- Desarrolló un protocolo rápido de hidrólisis asistida por microondas de dos fases para éteres de vinilo sustituidos por aminoácidos.
Conclusiones:
- El grupo dimetilamino dirige y acelera eficazmente las reacciones de multiarilación de Heck.
- Los métodos desarrollados proporcionan un acceso eficiente a los etanales diarilados y a las desoxibenzoinas sustituidas.
- La eliminación del grupo que dirige el catalizador es rápida y eficiente, simplificando el aislamiento del producto.
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