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Azidooxigenación electroquímica de alquenos mediada por un complejo de transferencia de carga TEMPO-N

Juno C Siu¹, Gregory S Sauer¹, Ambarneil Saha¹

¹Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.

Journal of the American Chemical Society

|August 31, 2018

Resumen

Un nuevo método electroquímico sintetiza eficientemente los compuestos C-O y C-N de los alquenos. Esta vía mediada por TEMPO implica un nuevo mecanismo de radicales de azidilo, que amplía las aplicaciones de la química sintética.

Área de la Ciencia:

Química orgánica
La electroquímica
Metodología sintética

Sus antecedentes:

La química de los radicales TEMPO (2,3-dimetil-2,3-dinitrobutano) es crucial en la síntesis orgánica.
Las reacciones mediadas por TEMPO a menudo implican diferentes vías mecanicistas.
El desarrollo de protocolos de difuncionalización suaves y eficientes para los alquenos sigue siendo un área de investigación activa.

Objetivo del estudio:

Para establecer un protocolo electroquímico suave y eficiente para la difuncionalización de alceno.
Para aclarar el mecanismo de reacción, en particular el papel de TEMPO y azida.
Explorar la utilidad sintética de los productos generados.

Principales métodos:

Síntesis electroquímica utilizando fuentes simples de alquenos y azidos.
Investigaciones mecanicistas detalladas, incluidos los cálculos de DFT y la caracterización espectroscópica.
Estudios cinéticos y mediciones del efecto del isótopo cinético.

Principales resultados:

Un nuevo protocolo electroquímico proporciona acceso a compuestos difuncionalizados de C-O y C-N.
Se descubrió un mecanismo de reacción distinto, que involucra un complejo de transferencia de carga TEMPO-N3 y la formación de radicales azidilo.
El paso que determina la velocidad implica la disociación reversible de TEMPO-N3 y la posterior adición de radicales a los alquenos.

Conclusiones:

El estudio presenta una nueva y eficiente vía electroquímica para la difuncionalización de alquenos.
Se aclaró un nuevo mecanismo para las reacciones mediadas por TEMPO que involucran radicales de azidilo.
Este descubrimiento amplía las aplicaciones sintéticas de la química de los radicales aminoxilo.

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