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Diazidación electroquímica catalizada por aminoácidos de alquenos mediada por un complejo de transferencia de carga
Juno C Siu1, Joseph B Parry1, Song Lin1
1Department of Chemistry and Chemical Biology , Cornell University , Ithaca , New York 14853 , United States.
Journal of the American Chemical Society
|January 24, 2019
Resumen
Un nuevo catalizador de radicales aminoxilo, CHAMPO, permite la diazidación electroquímica de alceno. Este método evita los metales de transición y los oxidantes, utilizando un complejo CHAMPO-N3 para una transferencia eficiente de grupos radicales.
Área de la Ciencia:
- Química orgánica
- La electroquímica
- Catálisis
Sus antecedentes:
- La diazidación tradicional de alquenos a menudo requiere condiciones duras, catalizadores de metales de transición o oxidantes estequiométricos.
- El desarrollo de métodos sostenibles y eficientes para la funcionalización de alquenos es un desafío clave en la síntesis orgánica.
Objetivo del estudio:
- Desarrollar un nuevo catalizador de radicales aminoxilo para la diazidación electroquímica de alquenos.
- Para lograr la diazidación sin depender de metales de transición o oxidantes químicos.
Principales métodos:
- Síntesis electroquímica utilizando un nuevo catalizador de radicales aminoxilo, el CHAMPO.
- Formación de un complejo de transferencia de carga CHAMPO-N3 generado anodicamente.
- Se probó una amplia gama de sustratos de alqueno.
Principales resultados:
- Se logró una diazidación electroquímica exitosa de una amplia gama de alquenos.
- La reacción procedió eficientemente sin catalizadores de metales de transición ni oxidantes químicos.
- Los estudios mecanicistas indicaron un doble papel catalítico para CHAMPO como agente oxidante y de transferencia de radicales.
Conclusiones:
- CHAMPO es un catalizador eficaz para la diazidación electroquímica de alquenos.
- Este método ofrece una alternativa más ecológica y eficiente a los protocolos de diazidación existentes.
- La doble función catalítica del radical aminoxilo es clave para el éxito de la reacción.
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