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Hidrogenación catalítica de los tioésteres, tiocarbamatos y tioamidas

Jie Luo, Michael Rauch, Liat Avram

Journal of the American Chemical Society

|December 17, 2020

Resumen

Los investigadores desarrollaron un nuevo catalizador de rutenio para la hidrogenación directa del tioester, produciendo alcoholes y tioles de manera eficiente y sin desperdicios. Este método supera los problemas de incompatibilidad del catalizador con los tiolos, ampliando la química de los compuestos organosulfurados.

Área de la Ciencia:

Química orgánica
Catálisis
Química ecológica

Sus antecedentes:

La hidrogenación directa de tioésteres a alcoholes y tioles es una vía de química verde deseable.
Los intentos anteriores se vieron obstaculizados por la incompatibilidad de los tiolos generados con los catalizadores de hidrogenación comunes.

Objetivo del estudio:

Desarrollar un método eficiente y selectivo para la hidrogenación directa de tioesters.
Para superar los problemas de envenenamiento por catalizadores asociados con los subproductos de tiol.

Principales métodos:

Utilizó un complejo de rutenio basado en acridina como catalizador.
Se realizó la hidrogenación directa de varios tioésteres utilizando gas H2 sin aditivos.
Investigó la hidrogenación de los tiocarbamatos y las tioamidas.

Principales resultados:

Se ha logrado una hidrogenación eficiente y selectiva de diversos tioesters a alcoholes y tioles.
Se ha demostrado una excelente tolerancia al grupo funcional, incluidos los grupos de amida, éster y ácido carboxílico.
Tiocarbamatos y tioamidas hidrogenados con éxito en condiciones similares.

Conclusiones:

El catalizador de rutenio desarrollado permite una síntesis fácil y libre de residuos de alcoholes y tioles a partir de tioésteres.
Esta metodología amplía significativamente el alcance de la hidrogenación de los compuestos organosulfurados.
La robustez del catalizador hacia los subproductos de tiol lo convierte en una herramienta valiosa en química sintética.

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