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Hidrogenación catalizada no metálica de los compuestos de carbonilo por hidrogenación de los compuestos de carbonilo

Daniel J Scott¹, Matthew J Fuchter, Andrew E Ashley

¹Department of Chemistry, Imperial College London , London SW7 2AZ, U.K.

Journal of the American Chemical Society

|October 22, 2014

Resumen

La hidrogenación catalítica libre de metales de cetonas y aldehídos se logra utilizando un ácido de Lewis, B ((C6F5) 3), en 1,4-dioxano. Este proceso utiliza un mecanismo de par de Lewis frustrado, destacando el disolvente.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

La hidrogenación catalítica tradicional de los grupos carbonilo a menudo se basa en metales preciosos o tóxicos.
El desarrollo de sistemas catalíticos libres de metales es un objetivo clave en la química sostenible.
Los ácidos de Lewis son catalizadores conocidos, pero su aplicación en la hidrogenación libre de metales es menos explorada.

Objetivo del estudio:

Investigar el potencial de los ácidos de Lewis como catalizadores para la hidrogenación libre de metales de los compuestos carbonílicos.
Para explorar el mecanismo de hidrogenación catalizada por B ((C6F5) 3) en 1,4-dioxano.
Establecer condiciones de reacción suaves para un proceso de hidrogenación catalítica completamente libre de metales.

Principales métodos:

Las soluciones utilizadas del ácido de Lewis tris (pentafluorofenil) borano (B (C6F5) 3) en 1,4-dioxano.
Probó la actividad catalítica para la hidrogenación de varias cetonas y aldehídos.
Investigó el mecanismo de reacción, identificando el papel del disolvente y el ácido de Lewis.

Principales resultados:

B(C6F5) 3 en 1,4-dioxano catalizó efectivamente la hidrogenación de diversas cetonas y aldehídos.
Logró la primera hidrogenación catalítica completamente libre de metales de grupos carboniles bajo condiciones suaves.
Se demostró que la reacción se produce a través de un mecanismo de par de Lewis frustrado que involucra al disolvente.

Conclusiones:

El Tris ((pentafluorofenil) borano es un catalizador eficaz para la hidrogenación libre de metales de los carbonilos.
El disolvente 1,4-dioxano juega un papel crucial en el mecanismo frustrado del par de Lewis.
Este trabajo abre nuevas vías para la hidrogenación catalítica sostenible y libre de metales.

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