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Reacciones de acoplamiento cruzado de electrófilos habilitadas por la protección de sobrecarga de

Blaise L Truesdell¹, Taylor B Hamby¹, Christo S Sevov¹

¹Department of Chemistry and Biochemistry, The Ohio State University, 151 West Woodruff Avenue, Columbus, Ohio 43210, United States.

Journal of the American Chemical Society

|March 3, 2020

Resumen

El acoplamiento electroquímico de electrófilos cruzados (XEC) ofrece una alternativa más ecológica a los métodos tradicionales. El uso de lanzaderas redox activas mejora la protección del catalizador, mejorando significativamente los rendimientos para aplicaciones amplias de sustrato.

Área de la Ciencia:

Química orgánica
La electroquímica
Catálisis

Sus antecedentes:

El acoplamiento electrofilo cruzado (XEC) convencional a menudo se basa en reductores estequiométricos.
Los métodos electroquímicos ofrecen potencial para una mayor reactividad y selectividad.
La protección de los catalizadores de la sobre-reducción es crucial para la síntesis electroquímica.

Objetivo del estudio:

Desarrollar una metodología electroquímica XEC impulsada mecanicamente.
Para utilizar lanzaderas redox activas para la protección del catalizador.
Para lograr XEC práctico, escalable y de amplia aplicación.

Principales métodos:

Reducción electroquímica.
Desarrollo de lanzaderas redox activas para la protección de sobrecarga.
Optimización de las condiciones de reacción para XEC.

Principales resultados:

Se han obtenido altos rendimientos (> 80%) de XEC utilizando transbordadores redox.
Se ha demostrado una amplia aplicabilidad a los bromuros de arilo, heteroarilo y vinilo con bromuros de alquilo.
Mostró escalabilidad en escalas multigramas con altas corrientes.

Conclusiones:

El XEC electroquímico con lanzaderas redox activas es una estrategia sintética práctica y escalable.
La protección de la sobrecarga es vital para el éxito de las metodologías electrosintéticas.
Este método proporciona una alternativa más ecológica y eficiente para la formación de enlaces C-C.

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