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2,2,2-Trichloroethyl aryldiazoacetates como reactivos robustos para la funcionalización C-H enantioselectiva de los

David M Guptill¹, Huw M L Davies

¹Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.

Journal of the American Chemical Society

|December 5, 2014

Resumen

Los investigadores desarrollaron nuevos catalizadores de rodio para la funcionalización C-H. Este método permite la inserción selectiva de C-H en éteres metílicos, logrando una alta enantioselectividad en la síntesis química.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

La funcionalización C-H es una transformación clave en la síntesis orgánica.
Desarrollar métodos selectivos y eficientes para la funcionalización C-H sigue siendo un desafío significativo.
Los carbenos intermedios de rodio (II) son especies reactivas versátiles para las reacciones de inserción C-H.

Objetivo del estudio:

Introducir una nueva clase de reactivos para la funcionalización C-H a través de la inserción de C-H.
Explorar el uso de nuevos intermediarios de carbenos sustituidos por el rodio (II) con donante/aceptor.
Para lograr la funcionalización C-H intermolecular enantioselectiva de los éteres de metilo.

Principales métodos:

Síntesis de 2,2,2-tricloroetil arilo y heteroarilo diazoacetatos.
Utilizando el catalizador de carboxilato de triarilciclopropano de dirodio Rh2(R-BPCP)4.
Realización de reacciones de inserción C-H intermoleculares con varios éteres metílicos.

Principales resultados:

Los reactivos y catalizadores desarrollados permitieron la funcionalización de C-H a través de la inserción de C-H.
Se observaron altos niveles de selectividad del sitio en la funcionalización de los éteres metílicos.
Se logró una excelente enantioselectividad en las reacciones de funcionalización C-H intermoleculares.

Conclusiones:

Se ha establecido un método novedoso y eficaz para la funcionalización C-H enantioselectiva.
La química desarrollada del rodio (II) carbeno ofrece una poderosa herramienta para la construcción de moléculas complejas.
Esta metodología es prometedora para aplicaciones en química medicinal y ciencia de materiales.

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