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Síntesis catalítica de arenas alquenílicas lineales "súper" utilizando un catalizador Rh (I) fácilmente preparado
Michael S Webster-Gardiner1, Junqi Chen1, Benjamin A Vaughan1
1Department of Chemistry, University of Virginia , Charlottesville, Virginia 22904, United States.
Journal of the American Chemical Society
|April 7, 2017
Resumen
Un nuevo catalizador de rodio permite la producción de alquilbenzenos lineales insaturados (LAB) a través de la vinilación oxidativa del areno, ofreciendo una ventaja sobre los productos saturados tradicionales. Este método logra una alta selectividad y eficiencia catalítica.
Área de la Ciencia:
- Química organometálica
- Catálisis
- Síntesis orgánica
Sus antecedentes:
- Los alquilbenzenos lineales (LAB) son sustancias químicas de importancia industrial.
- La síntesis tradicional de LAB se basa en la catálisis ácida, formando intermedios carbocationicos.
- La catálisis ácida impide inherentemente la formación de 1-fenilalcanos.
Objetivo del estudio:
- Desarrollar un nuevo método catalítico para la producción de alquilbenzenos lineales insaturados.
- Explorar el potencial de la catálisis del rodio en la funcionalización de arenas.
- Para superar las limitaciones de la producción tradicional de LAB catalizado por ácido.
Principales métodos:
- Utilizó un complejo de rodio, [Rh(μ-OAc) ((η2-C2H4) 2], como catalizador.
- Vinilación oxidativa del areno empleada para la síntesis de productos de alqueno sustituido por 1-fenilo.
- Se ha investigado la selectividad y la actividad catalítica en diversas condiciones.
Principales resultados:
- Se han logrado altas proporciones lineales a ramificadas (hasta 10:1).
- Se han demostrado altas pérdidas catalíticas superiores a 1470.
- Alquiló con éxito tanto los benzenos sustituidos con deficiencia de electrones como los ricos en electrones.
- Se han observado patrones de orto:meta:para selectividad distintos de la catálisis ácida.
Conclusiones:
- La vinilación oxidativa del areno catalizada por el rodio ofrece una nueva vía para los LAB insaturados.
- El método desarrollado presenta ventajas con respecto a la producción de areno alquilo saturado.
- El sistema catalítico exhibe un amplio alcance de sustrato y una regioselectividad única.
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