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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
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Reacciones de Aza-Matteson a través de inserciones controladas de mono y doble metileno en enlaces de nitrógeno y
1Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Journal of the American Chemical Society
|September 7, 2021
Resumen
Los investigadores desarrollaron reacciones de aza-Matteson para sintetizar aminas sustituidas por boro. Este método utiliza inserciones de carbenoides en enlaces de N-B, ofreciendo una nueva ruta a valiosos intermedios sintéticos.
Área de la Ciencia:
- Química orgánica
- Química sintética
Sus antecedentes:
- Las reacciones de homologación de boro, como la reacción de Matteson, son clave para crear alquilboronatos.
- Estas reacciones generalmente involucran inserciones de carbenoides en enlaces carbono-boro (C-B).
Objetivo del estudio:
- Desarrollar nuevas reacciones de aza-Matteson para sintetizar aminas sustituidas por boro.
- Para explorar las inserciones de carbenoides en los enlaces nitrógeno-boro (N-B) de los aminoboranos.
Principales métodos:
- Desarrollo de las reacciones de aza-Matteson utilizando la inserción de carbenoides en enlaces N-B.
- Variación sistemática de los grupos de salida de carbenoides y los activadores de ácido de Lewis.
- Aplicación a aminas secundarias comunes para la funcionalización selectiva.
Principales resultados:
- Síntesis exitosa de aminas terciarias sustituidas por α- y β-boro mediante inserciones selectivas de mono- y doble-metileno.
- Demostración de la derivación para moléculas bioactivas complejas que contienen aminas.
- Se ha logrado la diversificación de la funcionalidad de los productos de boronato y las inserciones secuenciales de carbenoides.
Conclusiones:
- Las reacciones de Aza-Matteson proporcionan un método eficiente y programable para acceder a diversas aminas sustituidas por boro.
- Este enfoque amplía la utilidad de las estrategias de homologación de boro a los compuestos que contienen nitrógeno.
- La metodología desarrollada ofrece vías versátiles para sintetizar valiosos intermedios sintéticos.
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