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Oxidación de alcohol aeróbico catalizado por hierro (III) nitrato/TEMPO: distinguir entre la cooperatividad redox en
Jordan E Nutting1, Kaining Mao1, Shannon S Stahl1
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Journal of the American Chemical Society
|July 7, 2021
Resumen
Este estudio revela un nuevo sistema de catalizador de hierro / aminoácido para la oxidación del alcohol, que demuestra "cooperación en serie" a través de una cascada redox. Esto difiere de los catalizadores de cobre, ofreciendo una nueva quimioselectividad en las reacciones de oxidación.
Área de la Ciencia:
- Catálisis
- Química orgánica
- Química inorgánica
Sus antecedentes:
- La catálisis cooperativa utilizando metales de transición y aminoxilos es clave para la oxidación del alcohol.
- Los sistemas de cobre/aminoxilo exhiben una "cooperatividad integrada" en la oxidación del alcohol.
- Los sistemas de hierro/aminoxilo presentan un mecanismo catalítico distinto.
Objetivo del estudio:
- Investigar el mecanismo de un nuevo sistema de catalizador de hierro/aminoxilo para la oxidación aeróbica del alcohol.
- Para proporcionar evidencia de "cooperación en serie" en el sistema catalizado por el hierro.
- Comparar las diferencias mecánicas entre los catalizadores a base de hierro y de cobre.
Principales métodos:
- Reacciones de oxidación del alcohol aeróbico.
- Cronometría en pasos cíclicos para la detección in situ de los productos intermedios.
- Investigación de los ciclos redox iniciados por el nitrato de hierro.
Principales resultados:
- Se encontraron pruebas de "cooperación en serie" en el sistema Fe/aminoxilo.
- Se detectó directamente una especie de oxoamonio como oxidante.
- Un ciclo redox basado en NO inicia la oxidación de aminoxilo/hidroxilamina a oxoamonio.
- Se observó una clara quimioselectividad y compatibilidad de grupos funcionales en comparación con los sistemas Cu/aminoxilo.
Conclusiones:
- El sistema de catalizador Fe/aminoxilo funciona a través de la "cooperatividad en serie", distinta de la "cooperatividad integrada" de los sistemas Cu/aminoxilo.
- Las diferencias mecánicas se atribuyen al ciclo redox basado en NO iniciado por el nitrato de hierro.
- Esto proporciona una nueva vía para la oxidación selectiva del alcohol con tolerancia de grupo funcional a medida.
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