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Oxidaciones alifáticas de C-H para la funcionalización en etapa tardía

M Christina White¹, Jinpeng Zhao¹

¹Roger Adams Laboratory, Department of Chemistry , University of Illinois at Urbana-Champaign , Urbana , Illinois 61801 , United States.

Journal of the American Chemical Society

|September 7, 2018

Resumen

Las reacciones de oxidación C-H no dirigidas permiten a los químicos modificar moléculas complejas en nuevos sitios. El ajuste del catalizador permite un control preciso de la oxidación, avanzando en las estrategias de funcionalización de última etapa.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La síntesis tradicional se basa en las características moleculares existentes para la funcionalidad.
La oxidación dirigida C-H extiende esta lógica, pero está limitada por la estructura del sustrato.
La oxidación C-H no dirigida ofrece una mayor flexibilidad sintética.

Objetivo del estudio:

Proporcionar una perspectiva histórica sobre los desafíos de la oxidación selectiva de C-H.
Para resaltar el descubrimiento y el impacto de la catálisis de hidroxilación no dirigida de C-H.
Demostrar el control de la selectividad del sitio a través del diseño del catalizador.

Principales métodos:

Revisión de las estrategias históricas de oxidación C-H.
Discusión de las hidroxilaciones alifáticas no dirigidas de C-H catalizadas por Fe (PDP).
Análisis de los factores electrónicos, estéricos y estéreoelectrónicos que influyen en la selectividad del sitio.

Principales resultados:

Demostró que los enlaces alifáticos C-H pueden oxidarse selectivamente sin dirigir grupos.
Reglas establecidas para predecir y controlar la selectividad del sitio en la oxidación C-H.
Se muestra la sintonización del catalizador (por ejemplo, Fe ((CF3-PDP)) para alterar el sitio de oxidación.

Conclusiones:

El desarrollo de la oxidación C-H no dirigida ha revolucionado la química sintética.
El control preciso de la selectividad del sitio se puede lograr mediante la modificación del catalizador.
Permite la funcionalización en etapa tardía para una diversificación eficiente de las moléculas.

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