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Síntesis de 2-ariloxi-1,3-dienes a partir de fenoles y carbonatos de propargilo

Naoki Ishida¹, Yusaku Hori¹, Shintaro Okumura¹

¹Department of Synthetic Chemistry and Biological Chemistry , Kyoto University , Katsura, Kyoto 615-8510 , Japan.

Journal of the American Chemical Society

|December 20, 2018

Resumen

Una nueva reacción catalizada por níquel sintetiza eficientemente valiosos 2-arioxi-1,3-dienos estereoselectivamente a partir de carbonatos y fenoles de propargilo. Este método ofrece una amplia tolerancia de grupo funcional y produce dienes útiles en diversas aplicaciones sintéticas, incluida la reacción de Diels-Alder.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los 1,3-dienos son componentes esenciales en la síntesis orgánica.
Los métodos existentes para sintetizar 1,3-dienos pueden carecer de eficiencia o de amplia aplicabilidad.
El desarrollo de rutas estereoselectivas hacia dienes funcionalizados es altamente deseable.

Objetivo del estudio:

Informar sobre un método nuevo y conveniente para la síntesis de 2-arioxi-1,3-dienos.
Lograr una síntesis estereoselectiva utilizando materiales de partida fácilmente disponibles.
Para demostrar la utilidad de los dienes sintetizados en futuras transformaciones químicas.

Principales métodos:

Reacción de acoplamiento catalizada por níquel entre carbonatos de propargilo y fenoles.
Optimización de las condiciones de reacción para lograr una alta estereoselectividad.
Caracterización de los 2-arioxi-1,3-dienos sintetizados y evaluación de la tolerancia del grupo funcional.

Principales resultados:

Síntesis exitosa y estereoselectiva de 2-arioxi-1,3-dienos.
Se observó una amplia tolerancia del grupo funcional, que acomodó grupos de yodo, formilo y boro.
Los dienos sintetizados son valiosos intermedios para las reacciones posteriores.

Conclusiones:

Se ha desarrollado un método conveniente y estereoselectivo catalizado por níquel para sintetizar 2-arioxi-1,3-dienos.
El método demuestra una excelente tolerancia de grupo funcional, ampliando su utilidad sintética.
Los 1,3-dienos resultantes son sintones versátiles, particularmente para las reacciones de Diels-Alder.

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