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Síntesis directa de las enamidas a través de la activación electrófila de las amidas

Philipp Spieß¹, Martin Berger¹, Daniel Kaiser¹

¹Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna, Austria.

Journal of the American Chemical Society

|July 7, 2021

Resumen

Los investigadores desarrollaron un nuevo método para convertir amidas en enamidas en un solo paso. Esta reacción eficiente utiliza el litio bis ((trimethylsil) amide y el anhídrido trifílico, ofreciendo un proceso simple con amplia aplicabilidad.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

Las amidas son grupos funcionales versátiles en la química orgánica.
Las enamidas son valiosos intermedios sintéticos con diversas aplicaciones.

Objetivo del estudio:

Informar sobre un nuevo método de un solo paso para la deshidrogenación de N de las amidas a las enamidas.
Introducir una nueva estrategia sintética que utilice reactivos fácilmente disponibles.

Principales métodos:

La reacción emplea el litio bis ((trimethylsil) amide (LiHMDS) y el anhídrido trifílico.
El anhídrido trifílico actúa como activador electrofílico y oxidante.
El proceso se caracteriza por una configuración experimental simple.

Principales resultados:

Se logró una nueva deshidrogenación en un solo paso de las amidas a las enamidas.
La reacción exhibe un amplio alcance de sustrato, lo que demuestra su versatilidad.
Las enamidas formadas se utilizaron con éxito en varias transformaciones aguas abajo.

Conclusiones:

Este estudio presenta un método eficiente y sencillo para sintetizar enamidas a partir de amidas.
El protocolo desarrollado ofrece una herramienta valiosa para la síntesis orgánica, permitiendo el acceso a diversas estructuras de enamida.

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