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Azidación radical descarboxilada por plata de ácidos carboxílicos alifáticos en solución acuosa

Chao Liu¹, Xiaoqing Wang¹, Zhaodong Li¹

¹†Key Laboratory of Organofluorine Chemistry and Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. China.

Journal of the American Chemical Society

|July 29, 2015

Resumen

Un nuevo método permite una azidación descarboxilada eficiente de ácidos carboxílicos alifáticos utilizando nitrato de plata y persulfato de potasio. Esta reacción produce azidas de alquilo en condiciones suaves con un amplio alcance de sustrato y tolerancia de grupo funcional.

Área de la Ciencia:

Química orgánica
Química sintética

Sus antecedentes:

Los ácidos carboxílicos alifáticos son bloques de construcción versátiles en la síntesis orgánica.
El desarrollo de métodos eficientes para la funcionalización, como la azidación, es crucial para crear nuevas moléculas.

Objetivo del estudio:

Informar sobre un método nuevo y general para la azidación descarboxilada de ácidos carboxílicos alifáticos.
Para explorar el alcance y las limitaciones de esta nueva ruta sintética.

Principales métodos:

Utilizando nitrato de plata (AgNO3) como catalizador y persulfato de potasio (K2S2O8) como oxidante.
Reaccionan diversos ácidos carboxílicos alifáticos con azida de tosilo o azida de piridina-3-sulfonilo en una solución acuosa de acetonitrilo (CH3CN).
Empleando condiciones de reacción suaves.

Principales resultados:

Síntesis exitosa de azidas alquilo correspondientes de varios ácidos carboxílicos alifáticos.
Demostrado amplio alcance de sustrato y excelente compatibilidad de grupo funcional.
Propuso un mecanismo radical para explicar el proceso de azidación específico del sitio.

Conclusiones:

El método desarrollado ofrece una vía eficiente y general para los alquilácidos.
La reacción se produce en condiciones suaves con una amplia aplicabilidad.
Los hallazgos contribuyen al avance de las metodologías sintéticas para la síntesis de azidas.

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