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Fluoración desconstructiva de aminas cíclicas mediante la escisión carbono-carbono
Jose B Roque1, Yusuke Kuroda1, Lucas T Göttemann1
1Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Science (New York, N.Y.)
|July 14, 2018
Resumen
Este estudio introduce la fluoración deconstructiva para la escisión de enlaces no tensados C{\displaystyle C} -C{\displaystyle C} en aminas cíclicas. Este nuevo método crea valiosos derivados de aminas mono y difluoradas a partir de piperidinas y pirrolidinas.
Área de la Ciencia:
- Química orgánica
- Química sintética
- Química de la fluoración
Sus antecedentes:
- Las funcionalizaciones deconstructivas suelen apuntar a los enlaces dobles carbono-carbono.
- El clivado y la funcionalización de los bonos C(sp3)-C(sp3) sin tensión siguen siendo un desafío con precedentes limitados.
- Los heterociclos de nitrógeno saturados como las piperidinas y las pirrolidinas son andamios importantes en la química medicinal.
Objetivo del estudio:
- Desarrollar una nueva estrategia de fluoración deconstructiva para la escisión de enlaces C(sp3) -C(sp3) en heterociclos de nitrógeno saturado.
- Para sintetizar derivados de aminas mono y difluoradas.
- Establecer las aminas cíclicas como sintones versátiles para los radicales aminoalquilo.
Principales métodos:
- Fluoración de apertura de anillos mediada por plata mediante el uso de Selectfluor.
- Aplicación a los heterociclos de nitrógeno saturado, incluidas las piperidinas y las pirrolidinas.
- Exploración de las estrategias de diversificación esquelética en etapa tardía.
Principales resultados:
- Fluoración exitosa de los enlaces C ((sp3) - C ((sp3)) en aminas cíclicas.
- Acceso a diversos derivados de aminas mono y difluoradas.
- Demostración de las aminas cíclicas como precursores de los radicales aminoalquilo.
Conclusiones:
- El método desarrollado proporciona una nueva ruta para la funcionalización de aminas cíclicas a través de la escisión de enlaces C ((sp3) -C ((sp3).
- Este enfoque permite la síntesis de bloques de construcción fluorados valiosos.
- La estrategia ofrece oportunidades para la diversificación en etapa tardía de las moléculas que contienen aminas.
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