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La borilación C-H catalizada por el hierro de los arenos

Thomas Dombray¹, C Gunnar Werncke^2,3, Shi Jiang¹

¹†Team Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, 263 av. du Général Leclerc, 35042 Rennes Cedex, France.

Journal of the American Chemical Society

|March 18, 2015

Resumen

Los catalizadores de hierro realizan eficientemente la borilación C-H de compuestos aromáticos utilizando pinacolborano bajo luz UV. Este estudio detalla el mecanismo catalítico e identifica las especies clave de hierro involucradas en la reacción.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los complejos de hierro ofrecen una alternativa sostenible a los catalizadores de metales preciosos.
La borilación C-H deshidrogenativa es una transformación clave para la introducción de grupos funcionales de boro.

Objetivo del estudio:

Para investigar los complejos de hierro bis (difosfina) como catalizadores para la borilación C-H.
Para aclarar el mecanismo catalítico de esta transformación.

Principales métodos:

Borilación C-H deshidrogenativa catalítica de compuestos aromáticos y heteroaromáticos utilizando catalizadores de hierro y pinacolborano.
La irradiación UV (350 nm) a temperatura ambiente. por ejemplo.
Estudios de reactividad estequiométrica y aislamiento de complejos intermedios de hierro.

Principales resultados:

Los complejos de hierro bis (difosfina) demostraron actividad en la borilación C-H.
Los productos borilados se obtuvieron en rendimientos moderados a buenos (25-73%) con una carga de catalizador de 5 mol%.
Se aisló y caracterizó un complejo de trans-hidrido (borilo) hierro, Fe (H) (Bpin) (dmpe) 2.

Conclusiones:

Los complejos de hierro son catalizadores eficaces para la borilación C-H deshidrogenativa de los compuestos (hetero) aromáticos.
El mecanismo propuesto destaca el papel de las especies catalizadoras clave del hierro.
Este trabajo proporciona información sobre las reacciones de borilación catalizadas por hierro.

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