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Arylación de las bencilaminas primarias y secundarias mediada por dióxido de carbono C (sp2) -H
Mohit Kapoor1, Pratibha Chand-Thakuri1, Michael C Young1
1Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering , University of Toledo , Toledo , Ohio 43606 , United States.
Journal of the American Chemical Society
|April 30, 2019
Resumen
Este estudio introduce un nuevo método catalizado por el paladio que utiliza dióxido de carbono (CO2) para crear bencilaminas orto-ariladas. Esta eficiente estrategia de formación de enlaces C-C funciona bajo condiciones suaves, dando como resultado productos de aminas directamente utilizables.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- La activación de C-H catalizada por metales de transición es una estrategia clave para la formación de enlaces C-C.
- La síntesis de orto-arilbenzilaminas es farmacológicamente importante pero desafiante, especialmente para las benzilaminas primarias y secundarias libres que utilizan Palladium (II).
Objetivo del estudio:
- Desarrollar una estrategia eficaz para la formación de enlaces orto-C-C de las benzilaminas primarias y secundarias libres.
- Utilizar el dióxido de carbono (CO2) como mediador en la orto-arilación catalizada por el paladio.
Principales métodos:
- La orto-arilación catalizada por el paladio de las benzilaminas primarias y secundarias libres.
- Inclusión de dióxido de carbono (CO2) para facilitar la reacción en condiciones suaves.
- Estudios mecanicistas para aclarar el papel del CO2 en la etapa de determinación de la velocidad.
Principales resultados:
- Se estableció una nueva estrategia para la construcción de benzilaminas primarias y secundarias orto-arilladas mediadas por CO2.
- La reacción se lleva a cabo en condiciones relativamente suaves debido al papel crítico del CO2.
- Las temperaturas más suaves producen productos de aminas libres, eliminando la necesidad de desprotección.
- Se logró una monoarilación selectiva en casos de diarilación potencial, atribuida a un efecto quelante.
Conclusiones:
- El método desarrollado, mediado por el CO2 y catalizado por el paladio, ofrece una vía eficiente para obtener valiosas benzilaminas orto-ariladas.
- La estrategia proporciona productos directamente utilizables bajo condiciones suaves, simplificando los procedimientos sintéticos.
- Los hallazgos avanzan en las metodologías de activación de C-H y ofrecen un enfoque práctico para importantes andamios de aminas.
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