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Acceso directo a electrófilos versátiles mediante cianado oxidativo catalítico de alquenos
De-Wei Gao1, Ekaterina V Vinogradova2, Sri Krishna Nimmagadda1
1Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Journal of the American Chemical Society
|June 13, 2018
Resumen
Este estudio introduce un nuevo método catalizado por el cobre para la cianuración oxidativa de alquenos, creando valiosos nitriles de alquenilo ramificados. Estos compuestos son útiles para la síntesis orgánica y el descubrimiento de ligandos de proteínas covalentes en el descubrimiento de fármacos.
Área de la Ciencia:
- Química orgánica
- Catálisis
- Biología Química
Sus antecedentes:
- El ataque nucleófilo a los electrófilos de carbono es fundamental en química y biología.
- El ajuste de las propiedades electrófilas es clave para la síntesis orgánica y el descubrimiento de fármacos.
- Es muy deseable desarrollar métodos para convertir materias primas simples en electrófilos versátiles.
Objetivo del estudio:
- Desarrollar un método catalítico para la oxidación regioselectiva de alquenos.
- Para sintetizar nitriles alquenilo ramificados, que son difíciles de acceder a través de los métodos actuales.
- Demostrar la utilidad de los nitriles de alqueno sintetizados en la síntesis orgánica y la proteómica química.
Principales métodos:
- Se empleó catálisis de cobre homogéneo para la reacción de cianado oxidativo.
- Se utilizó un oxidante nitrógeno-fluoro (N-F) junto con el catalizador de cobre.
- La reacción se aplicó tanto a alquenos conjugados como no conjugados.
Principales resultados:
- Se logró una oxidación catalítica y regioselectiva de los alquenos.
- Se han sintetizado con éxito los nitriles de alquenilo ramificados.
- Se demostró que los productos eran socios electrófilos efectivos en reacciones posteriores.
Conclusiones:
- El método desarrollado proporciona acceso a nitriles de alqueno ramificados valiosos a partir de alquenos simples.
- Estos nitriles son versátiles bloques de construcción para la síntesis orgánica.
- El estudio destaca el potencial de estos compuestos en el descubrimiento proteómico químico de los ligandos de proteínas covalentes.
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