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Ferro ((II) - Aminofluoración intermolecular catalizada de las olefinas no funcionalizadas utilizando el ion fluoruro

Deng-Fu Lu¹, Cheng-Liang Zhu¹, Jeffrey D Sears¹

¹Department of Chemistry, Georgia State University , 100 Piedmont Avenue SE, Atlanta, Georgia 30303, United States.

Journal of the American Chemical Society

|August 17, 2016

Resumen

Un nuevo método catalizado por el hierro permite la aminofluoración de olefinas para diversas olefinas, obteniendo valiosos fluorocarbamatos. Este avance ofrece una nueva ruta para sintetizar moléculas orgánicas complejas anteriormente inaccesibles.

Área de la Ciencia:

Química orgánica
Catálisis
Química de la fluoración

Sus antecedentes:

La aminofluoración de las olefinas es crucial para la síntesis de compuestos orgánicos fluorados.
Los métodos existentes a menudo luchan con las olefinas no funcionalizadas y no estirenil.
El desarrollo de sistemas catalíticos eficientes y selectivos sigue siendo un desafío clave.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para la fluoración intermolecular de las olefinas.
Para utilizar catalizadores de hierro en abundancia en la tierra para esta transformación.
Ampliar el alcance del sustrato para incluir olefinas desafiantes no funcionalizadas y no estirenil.

Principales métodos:

Utilizando catalizadores de hierro abundantes en la tierra con iones de fluoruro nucleófilo.
Reaccionan con una amplia gama de olefinas no funcionalizadas y no estirenil.
Investigando los estudios mecanicistas preliminares incluyendo la inducción asimétrica.

Principales resultados:

Se ha logrado la fluoración intermolecular de las olefinas mediante la catálisis del hierro.
Alta regioselectividad (N frente a F) en la formación de fluorocarbamatos en las proximidades.
Tolerancia demostrada a diversas olefinas, incluidos los tipos no estirenilo incompatibles con los métodos anteriores.
Potencial para la inducción asimétrica utilizando catalizadores de hierro quirales.

Conclusiones:

Se ha establecido un nuevo y eficiente método catalizado por el hierro para la aminofluoración de olefinas.
Este método proporciona acceso a valiosos fluorocarbamatos de las olefinas fácilmente disponibles.
El proceso ofrece un mejor alcance de sustrato y potencial para la síntesis estereoselectiva.

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