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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
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Cianización asimétrica de radicales propárgicos habilitada por la doble organofotorredox y la catálisis del cobre
Fu-Dong Lu1, Dan Liu1, Lei Zhu2
1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry , Central China Normal University , 152 Luoyu Road , Wuhan 430079 , China.
Journal of the American Chemical Society
|April 2, 2019
Resumen
Este estudio introduce la primera cianización asimétrica de radicales propárgicos mediante doble fotorreducción y catálisis de cobre. El método produce eficientemente cianuros de propargilo ópticamente activos con alta enantioselectividad.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Síntesis asimétrica
Sus antecedentes:
- Los cianuros propargílicos son productos intermedios sintéticos muy valiosos.
- La cianificación asimétrica de los radicales propargílicos sigue siendo un desafío.
Objetivo del estudio:
- Desarrollar el primer método enantioselectivo para la cianización de radicales propárgicos.
- Para lograr altos rendimientos y enantioselectividades en la síntesis de cianuros de propargilo ópticamente activos.
Principales métodos:
- Catálisis dual que emplea un fotocatalizador orgánico y un complejo quiral de cobre.
- Generación de radicales de propargilo a través de la catálisis fotorredóxica.
- Cianización enantioselectiva mediada por el catalizador quiral de cobre.
Principales resultados:
- Síntesis exitosa de varios cianuros de propargilo ópticamente activos.
- Se obtienen altos rendimientos de reacción (57-97%) y enantioselectividades (83-98% ee).
- Demostró la amplia aplicabilidad de la reacción con 28 ejemplos.
Conclusiones:
- El sistema catalítico dual desarrollado es altamente eficaz para la cianización de radicales propárgicos asimétricos.
- Los estudios mecánicos proporcionan información sobre la vía de reacción y el control estereoquímico.
- Este trabajo ofrece una nueva ruta a valiosos compuestos de cianuro propárgico quiral.
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