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Carboaminación de tres componentes de alquenos catalizados por cu
Samuel N Gockel1, Travis L Buchanan1, Kami L Hull1
1Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.
Journal of the American Chemical Society
|November 3, 2017
Resumen
Este estudio introduce una reacción de carboaminación catalizada por el cobre para crear compuestos aminos valiosos a partir de alquenos y α-halocarbonilos. El método funciona eficientemente varios alquenos y aminas, ofreciendo una nueva vía sintética.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Metodología sintética
Sus antecedentes:
- La carboaminación intermolecular de alquenos es una transformación crucial para la síntesis de compuestos que contienen nitrógeno.
- El desarrollo de sistemas catalíticos eficientes para la formación de enlaces C-N sigue siendo un área activa de investigación.
Objetivo del estudio:
- Desarrollar una nueva carboaminación intermolecular catalizada por el cobre de alquenos utilizando α-halocarbonilos y aminas.
- Demostrar el amplio alcance del sustrato y la eficacia del método desarrollado.
Principales métodos:
- Reacción catalizada por el cobre de alquenos (estirenos, α-olefinas) con α-halocarbonilos y varias aminas.
- Exploración de estirenos ricos en electrones, pobres en electrones y estirenos internos, así como de las α-olefinas.
- Estudios mecanicistas que incluyen radicales intermedios y especies de oxocarbenio.
Principales resultados:
- Se logró con éxito la carboaminación intermolecular catalizada por cobre de diversos alquenos con α-halocarbonilos y aminas.
- Demostró la aplicabilidad de la reacción a una amplia gama de sustratos, incluidos los estirenos ricos en electrones, pobres en electrones y internos, junto con las α-olefinas.
- Identificó un mecanismo de reacción plausible que involucra la adición radical centrada en el carbono, la oxidación y la apertura del anillo nucleófilo.
Conclusiones:
- La carboaminación catalizada por cobre desarrollada proporciona una ruta efectiva para sintetizar aminas funcionalizadas.
- La reacción exhibe un amplio alcance de sustrato y ofrece una herramienta valiosa para la síntesis orgánica.
- Las ideas mecánicas arrojan luz sobre la formación del enlace C-N a través de una nueva vía.
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