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El hierro cataliza la hidrogenación asimétrica de las cetonas

Yanyun Li¹, Shenluan Yu, Xiaofeng Wu

¹State Key Laboratory of Physical Chemistry of Solid Surfaces, National Engineering Laboratory for Green Chemical Productions of Alcohols, Ethers, and Esters, College of Chemistry and Chemical Engineering, Xiamen University , Xiamen 361005, P. R. China.

Journal of the American Chemical Society

|February 15, 2014

Resumen

Este estudio introduce un nuevo catalizador de hierro para la hidrogenación asimétrica de cetonas, ofreciendo una alternativa sostenible a los catalizadores de metales preciosos. Este método logra altos rendimientos y pureza óptica para los valiosos alcoholes quirales.

Área de la Ciencia:

La catálisis es la catálisis.
Química orgánica es la química orgánica.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Los alcoholes quirales son bloques de construcción esenciales en productos farmacéuticos, agroquímicos y productos químicos finos.
La hidrogenación asimétrica (AH) es un proceso industrial clave para producir moléculas quirales, predominantemente utilizando catalizadores de rodio, rutenio o iridio.
Desarrollar catalizadores rentables y sostenibles para el AH sigue siendo un desafío importante.

Objetivo del estudio:

Desarrollar un catalizador industrialmente viable y rentable para la hidrogenación asimétrica de cetonas.
Para demostrar la eficacia de un sistema de catalizador basado en hierro como una alternativa a los catalizadores de metales nobles.
Para lograr un alto rendimiento y enantioselectividad en la producción de alcoholes quirales.

Principales métodos:

Síntesis de un ligando macrocíclico quiral de 22 miembros.
Complejación del ligando con el precursor del hierro Fe3(CO)12 para formar el catalizador de hierro.
Hidrogenación asimétrica de varias cetonas utilizando el catalizador de hierro bajo 50 bar H2 a 45-65 °C.

Principales resultados:

El catalizador de hierro desarrollado hidrogenó efectivamente una amplia gama de cetonas.
Se lograron altas enantioselectividades, comparables o superiores a los catalizadores de metales nobles, para los alcoholes quirales resultantes.
El proceso de hidrogenación catalizado por hierro exhibió características de heterogeneidad, diferenciándolo del típico AH. catalizado por metales nobles.

Conclusiones:

Se ha desarrollado con éxito un catalizador de hierro simple e industrialmente viable para la hidrogenación asimétrica de cetonas.
Este catalizador de hierro proporciona una alternativa sostenible y rentable a los catalizadores de metales preciosos para la producción de valiosos alcoholes quirales.
La naturaleza heterogénea del catalizador de hierro ofrece ventajas potenciales para la separación y el reciclaje de catalizadores en aplicaciones industriales.

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