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Desfuncionalización catalítica del 1,3- a través de la activación oxidativa del enlace C-C

Steven M Banik¹, Katrina M Mennie¹, Eric N Jacobsen¹

¹Department of Chemistry & Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.

Journal of the American Chemical Society

|June 18, 2017

Resumen

Los investigadores desarrollaron un método catalítico general para la oxidación de 1,3-ciclopropanos, lo que permite un control preciso de la conformación molecular a través de la introducción de sustitutos electronegativos como el flúor.

Área de la Ciencia:

Química orgánica
Catálisis
Estereoquímica

Sus antecedentes:

Los sustituyentes electronegativos en las relaciones 1,3 influyen en la conformación molecular a través de la minimización del dipolo.
El desarrollo de métodos generales para incorporar estas relaciones es crucial para la modulación de la forma molecular.

Objetivo del estudio:

Establecer una estrategia general para la oxidación del 1,3-ciclopropano.
Para explorar la aplicación de esta estrategia en las reacciones de 1,3-difluoración.
Para demostrar la utilidad de los compuestos sintetizados en el control de la conformación molecular.

Principales métodos:

Se utilizó la catálisis del yodo arilo (I-III) para la apertura oxidativa del anillo de los ciclopropanos.
Se utilizan reactivos prácticos disponibles en el mercado para las reacciones.
Investigó una variedad de sustratos de ciclopropano sustituidos.

Principales resultados:

Se ha conseguido una eficiente difluoración de los ciclopropanos.
Sintetizó diversos productos 1,3-difuncionalizados, incluidos los 1,3-fluoroacetoxilatos, los 1,3-diolos, los 1,3-aminoalcoholes y las 1,3-diaminas.
Se confirmó la influencia conformacional de los 1,3-difluoruros a través del análisis estructural.

Conclusiones:

La estrategia catalítica descrita proporciona una vía versátil para la difuncionalización de 1,3-ciclopropanos.
Este método ofrece una herramienta valiosa para controlar la conformación molecular.
El enfoque es general y aplicable a varios derivados del ciclopropano.

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