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Síntesis de alcohol por hidroformilación reductora impulsada por luz visible catalizada por cobalto
Connor S MacNeil1, Lauren N Mendelsohn1, Tyler P Pabst1
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
Journal of the American Chemical Society
|October 14, 2022
Resumen
Los catalizadores de cobalto permiten la hidroformilación reductora de alquenos utilizando monóxido de carbono e hidrógeno. Este proceso produce alcoholes anti-Markovnikov con alta regioselectividad, ofreciendo una nueva ruta sintética.
Área de la Ciencia:
- Química organometálica
- Catálisis
- Síntesis orgánica
Sus antecedentes:
- La hidroformilación es un proceso industrial clave para la conversión de alquenos en aldehídos.
- El desarrollo de sistemas catalíticos selectivos y eficientes sigue siendo un área activa de investigación.
- La hidroformilación reductora ofrece una ruta directa a los alcoholes, evitando el aislamiento del aldehído.
Objetivo del estudio:
- Describir una nueva hidroformilación reductora catalizada por cobalto de alquenos.
- Lograr un alto rendimiento y un control regional exclusivo en la síntesis de alcoholes homologados de un solo carbono.
- Investigar el mecanismo catalítico y los orígenes de la regioselectividad.
Principales métodos:
- Utilizando un complejo de hidruro de cobalto, (dcype) Co (CO) 2 H, activado por la irradiación de luz azul.
- Utilizando gas de síntesis (CO y H2) como fuente de monóxido de carbono e hidrógeno.
- Espectroscopia de RMN multinuclear in situ para las investigaciones mecanicistas.
Principales resultados:
- Síntesis exitosa de alcoholes homologados de un carbono a partir de alquenos terminales y 1,1-disubstituidos.
- Logró la formación de productos anti-Markovnikov con rendimientos que oscilan entre el 34 y el 87%.
- Se ha demostrado un control regional exclusivo (lineal/de ramificación > 99:1) para alquenos mínimamente funcionalizados.
Conclusiones:
- El sistema de catalizador de cobalto desarrollado proporciona un método eficiente para la hidroformilación reductora.
- El estudio aclara la base mecanicista del regiocontrol absoluto observado.
- Este trabajo presenta una nueva herramienta valiosa para la síntesis de alcoholes funcionalizados.
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