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Los ligandos bis-N-heterocíclicos de carbenos aminopincer permiten una alta actividad en la hidrogenación de ésteres

Georgy A Filonenko, Mae Joanne B Aguila¹, Erik N Schulpen

¹§DSM Innovative Synthesis BV, P.O. Box 18, 6160 MD Geleen, The Netherlands.

Journal of the American Chemical Society

|June 9, 2015

Resumen

Los ligantes de aminopincer de carbenos bis-N-heterocíclicos (NHC) permiten una hidrogenación catalítica eficiente de los ésteres a los alcoholes. Este nuevo sistema logra una alta actividad a baja carga de rutenio, ofreciendo una alternativa prometedora a los catalizadores tradicionales.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis es la catálisis.
Química verde es la química verde.

Sus antecedentes:

La hidrogenación de ésteres es crucial para la producción de alcoholes.
Los métodos convencionales a menudo se basan en ligandos de fosfina, que pueden ser sensibles y costosos.
Se necesita el desarrollo de sistemas catalíticos nuevos, robustos y eficientes.

Objetivo del estudio:

Para introducir ligandos de aminopincer de carbenos bis-N-heterocíclicos (NHC) para la hidrogenación de ésteres.
Para sintetizar y caracterizar un nuevo complejo de rutenio-NHC.
Para evaluar el rendimiento catalítico del nuevo sistema.

Principales métodos:

Síntesis de los ligandos del aminopincer bis-NHC.
Aislamiento y caracterización de un complejo dimérico de rutenio, [Ru2(L) 2Cl3]PF6.6.
Hidrogenación catalítica de varios ésteres utilizando el complejo de rutenio.

Principales resultados:

El complejo de rutenio dimérico demostró una alta actividad catalítica en la hidrogenación de ésteres.
Se lograron actividades iniciales de hasta 283.000 h-1 a 12,5 ppm de carga de rutenio para la hidrogenación de hexanoato de etilo.
Convirtió con éxito un amplio espectro de ésteres alifáticos y aromáticos a sus correspondientes alcoholes en altos rendimientos.

Conclusiones:

Los ligandos de aminopincer bis-NHC representan una nueva y efectiva clase de catalizadores para la hidrogenación de ésteres.
El sistema catalítico desarrollado ofrece una alta eficiencia y un amplio alcance de sustrato.
Este enfoque proporciona una alternativa atractiva y estable en el aire a los sistemas catalíticos convencionales basados en fosfina.

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