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Síntesis de sulfonamidas mediante el acoplamiento electroquímico oxidativo de aminas y tiolos

Gabriele Laudadio¹, Efstathios Barmpoutsis¹, Christiane Schotten^1,2

¹Micro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry , Eindhoven University of Technology , Het Kranenveld, Bldg 14 - Helix , 5600 MB Eindhoven , The Netherlands.

Journal of the American Chemical Society

|March 26, 2019

Resumen

Este estudio introduce una síntesis electroquímica ecológica para las sulfonamidas, acoplando directamente los tiolos y las aminas en solo cinco minutos. Este método evita reactivos y catalizadores agresivos, produciendo sólo hidrógeno como subproducto.

Área de la Ciencia:

Química orgánica
Química ecológica
La electroquímica

Sus antecedentes:

Las sulfonamidas son unidades estructurales cruciales en los productos farmacéuticos y agroquímicos.
El desarrollo de rutas sintéticas eficientes y sostenibles para las sulfonamidas es una prioridad de investigación en curso.

Objetivo del estudio:

Desarrollar un nuevo método electroquímico ecológicamente benigno para la síntesis de sulfonamidas.
Para lograr el acoplamiento oxidativo de tiolos y aminas utilizando la electricidad como la única fuerza motriz.

Principales métodos:

Se empleó una reacción de acoplamiento oxidativo electroquímica entre tiolos y aminas.
La reacción se llevó a cabo utilizando productos químicos de fácil acceso y de bajo costo.
El proceso fue optimizado para la velocidad, logrando la finalización en sólo 5 minutos.

Principales resultados:

La transformación es totalmente impulsada por electricidad, eliminando la necesidad de reactivos de sacrificio o catalizadores adicionales.
El gas hidrógeno se genera como un subproducto limpio en el electrodo de contador.
La reacción exhibe un amplio alcance de sustrato y una excelente tolerancia de grupo funcional debido a condiciones leves.

Conclusiones:

Este enfoque electroquímico ofrece un método rápido, sostenible y eficiente para la síntesis de sulfonamidas.
La metodología descrita representa un avance significativo en la química sintética verde para acceder a compuestos de sulfonamidas valiosos.

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