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La fluoración descarboxilativa de los ácidos carboxílicos alifáticos a través de la catálisis fotorredóxica

Sandrine Ventre¹, Filip R Petronijevic¹, David W C MacMillan¹

¹Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society

|April 18, 2015

Resumen

La catálisis de luz visible permite la conversión directa de ácidos carboxílicos en fluoruros de alquilo. Este método simple y neutro en redox produce fluoroalcanos de manera eficiente a través de intermediarios de radicales carboxilo.

Área de la Ciencia:

Química orgánica es la química orgánica.
La fotocatálisis por fotocatálisis.

Sus antecedentes:

La fluoración directa de los ácidos carboxílicos alifáticos sigue siendo un reto.
El desarrollo de métodos de fluoración eficientes y versátiles es crucial en la síntesis orgánica.

Objetivo del estudio:

Desarrollar un nuevo método para la conversión directa de ácidos carboxílicos alifáticos en fluoruros de alquilo.
Para utilizar la catálisis fotorredóxica de luz visible para esta transformación.

Principales métodos:

La catálisis fotorredóxica promovida por la luz visible.
Oxidación de carboxilatos para generar radicales carboxilo.
La extrusión de CO2 y la posterior transferencia de F (((•) a partir de un reactivo fluorado.

Principales resultados:

Conversión directa exitosa de varios ácidos carboxílicos alifáticos a fluoruros de alquilo.
Se ha demostrado una alta eficiencia y un amplio alcance de sustrato.
Condiciones de reacción operacionalmente simples y neutras en redox.

Conclusiones:

La catálisis fotorredóxica de luz visible ofrece una ruta eficiente a los fluoruros de alquilo de los ácidos carboxílicos.
El método procede a través de una vía de enfriamiento oxidativo que involucra radicales carboxilo.
Este protocolo proporciona una herramienta valiosa para la introducción de flúor en moléculas orgánicas.

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