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Métodos eficientes y selectivos catalizados por Cu/nitroxilo para la lactonización oxidativa aeróbica de diolos
Xiaomin Xie1, Shannon S Stahl1
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Journal of the American Chemical Society
|March 10, 2015
Resumen
Los nuevos catalizadores de cobre/nitroxilo permiten una lactonización oxidativa aeróbica eficiente de los diolos utilizando aire. La elección del catalizador ajusta la selectividad para varios tipos de diol, ofreciendo una amplia compatibilidad con el alcohol y tolerancia al grupo funcional.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- La catálisis de la catálisis.
- Química verde es la química verde.
Sus antecedentes:
- La lactonización oxidativa es una transformación crucial en la síntesis orgánica.
- Desarrollar sistemas catalíticos eficientes y selectivos para esta reacción sigue siendo un desafío.
- Es muy deseable utilizar el aire ambiente como un oxidante sostenible.
Objetivo del estudio:
- Identificar nuevos sistemas de catalizadores de cobre/nitroxilo para la lactonización oxidativa aeróbica de los diolos.
- Investigar la influencia de la identidad del cocatalizador de nitróxilo en la selectividad de la reacción.
- Establecer el alcance y las limitaciones de estos sistemas catalíticos.
Principales métodos:
- Se realizaron reacciones de lactonización oxidativa aeróbica utilizando varios diolos.
- Los catalizadores de cobre fueron emparejados con diferentes cocatalizadores de nitroxilo, específicamente 9-azabiciclo[3.3.1]nonan-N-oxyl (ABNO) y 2,2,6,6-tetrametil-1-piperidinyl-N-oxyl (TEMPO).
- Las condiciones de reacción fueron optimizadas para la eficiencia y la selectividad.
Principales resultados:
- Se logró una lactonización oxidativa aeróbica altamente eficiente y selectiva de los diolos en condiciones suaves.
- El sistema Cu/ABNO demostró una excelente reactividad con diolos simétricos e impedidos no simétricos.
- El sistema Cu/TEMPO exhibió una quimio- y regioselectividad superior para diolos asimétricos menos obstaculizados.
- Los sistemas de catalizadores mostraron compatibilidad con diversas clases de alcohol (bencílico, alílico, alifático) y grupos funcionales (alquenos, heterociclos).
Conclusiones:
- Los nuevos catalizadores de Cu/nitroxilo proporcionan una poderosa plataforma para la lactonización oxidativa aeróbica.
- La quimio- y regioselectividad ajustable se puede lograr mediante una selección juiciosa del cocatalizador de nitróxilo.
- Estos métodos ofrecen un enfoque sostenible y versátil para sintetizar lactonas a partir de diolos.
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