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Hidrocarboxilación de alquinos impulsada por la luz visible utilizando CO2 a través de la catálisis dual de iridio y
Jing Hou1, Aloysius Ee1, Wei Feng1
1Department of Chemistry , National University of Singapore , 3 Science Drive 3 , Republic of Singapore 117543.
Journal of the American Chemical Society
|March 30, 2018
Resumen
Este estudio introduce la doble catálisis impulsada por luz visible para la funcionalización de alquinos utilizando dióxido de carbono (CO2). El nuevo método sintetiza de manera eficiente los heterociclos farmacéuticamente relevantes y los γ-hidroxibutenolidos en un solo recipiente.
Área de la Ciencia:
- Química orgánica
- Catálisis
- La fotoquímica
Sus antecedentes:
- La difuncionalización de alquinas es crucial para la síntesis de moléculas orgánicas complejas.
- El uso de dióxido de carbono (CO2) como fuente de C1 es significativo desde el punto de vista ambiental.
- La fotocatálisis con luz visible ofrece un enfoque sostenible para las transformaciones químicas.
Objetivo del estudio:
- Desarrollar un nuevo sistema catalítico dual impulsado por luz visible para la hidrocarboxilación de alquinos y la carbocarboxilación.
- Para sintetizar de manera eficiente los heterociclos farmacéuticamente importantes y los γ-hidroxibutenolidos a partir de las alquinas y el CO2.
- Explorar nuevas estrategias en cascada para la difuncionalización de alquinos y alquenos.
Principales métodos:
- Utilizando un sistema catalítico dual de iridio y cobalto bajo irradiación de luz visible.
- Utilizando alquinas y dióxido de carbono fácilmente disponibles como materiales de partida.
- Un procedimiento de un solo recipiente que implica la hidrocarboxilación, la isomerización de alquenos, la ciclización y las reacciones en cascada.
Principales resultados:
- Se ha logrado la hidrocarboxilación y la carbocarboxilación de los alquinos mediante CO2 con luz visible.
- Síntesis directa de cumarinas, 2-quinolonas y 2-benzoxepinonas a través de una secuencia de una vasija.
- Síntesis eficiente de γ-hidroxibutenolides a través de una cascada de migración de cobalto y acilo sin precedentes.
- Se ha demostrado la doble función del fotocatalizador de iridio en la transferencia de un solo electrón y la transferencia de energía.
Conclusiones:
- La catálisis dual desarrollada proporciona una ruta versátil y eficiente a heterociclos valiosos y otras moléculas funcionalizadas.
- Este trabajo establece una nueva estrategia en cascada para la difuncionalización de alquinas, expandiendo las posibilidades sintéticas.
- La metodología ofrece un enfoque sostenible y práctico utilizando luz visible y CO2.
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