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Acoplamientos transversalmente electrófilos de sales de tetraalquilo amonio impulsados por luz visible y libres de
Li-Li Liao1, Guang-Mei Cao1, Jian-Heng Ye1
1Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , People's Republic of China.
Journal of the American Chemical Society
|December 7, 2018
Resumen
Este estudio introduce el primer acoplamiento electrófilo cruzado sin reductores externos utilizando la catálisis fotorredóxica con luz visible. El subproducto de la trimetilamina actúa como donante de electrones, permitiendo la formación selectiva de enlaces C-C en condiciones suaves.
Área de la Ciencia:
- Química orgánica
- Fotocatálisis
- Metodología sintética
Sus antecedentes:
- Los acoplamientos electrofílicos cruzados son vitales para la formación de enlaces C-C, pero generalmente requieren reductores estequiométricos.
- El desarrollo de métodos de acoplamiento más económicos y sostenibles es un desafío clave en la síntesis orgánica.
Objetivo del estudio:
- Establecer la primera estrategia de acoplamiento de electrófilos cruzados sin reductores externos.
- Para utilizar la catálisis fotorredóxica de luz visible para la formación eficiente de enlaces C-C.
- Utilizar subproductos generados in situ como donantes de electrones.
Principales métodos:
- Catalización por fotorreducción con luz visible.
- Acoplamiento de sales de tetraalquilo amonio con aldehídos/cetonas y dióxido de carbono.
- Utilizando trimetilamina como un donante de electrones generado in situ.
Principales resultados:
- Se ha logrado el acoplamiento transversal electrofilo sin reductores externos.
- Amplio alcance del sustrato, incluidos los enlaces C-N primarios, secundarios y terciarios.
- Se han demostrado condiciones de reacción leves, baja carga del catalizador y buena tolerancia del grupo funcional.
- Escalabilidad del protocolo confirmada.
Conclusiones:
- Se ha desarrollado un método novedoso y sostenible para el acoplamiento electrofilo cruzado.
- Este protocolo ofrece una alternativa más ecológica a los métodos tradicionales al eliminar los reductores externos.
- Las perspectivas mecanicistas sugieren que los radicales bencílicos y los aniones son intermediarios clave, abriendo nuevas vías en la investigación de acoplamiento electrófilo cruzado.
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