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Sililación deshidrogenativa catalizada por el manganeso de alquenos siguiendo dos vías paralelas de la esfera interna

Stefan Weber¹, Manuel Glavic¹, Berthold Stöger²

¹Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria.

Journal of the American Chemical Society

|October 13, 2021

Resumen

Desarrollamos una silición deshidrogenativa de alquenos catalizada por el manganeso (I) sin aditivos utilizando un precatalizador de alquilo bisfosfina estable. Este método produce eficazmente los vinilsilanos y los alilsilanos a temperatura ambiente.

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Área de la Ciencia:

Química organometálica
Catálisis
Síntesis orgánica

Sus antecedentes:

La silición deshidrogenativa es una transformación clave para la síntesis de compuestos organosilicones.
El desarrollo de sistemas catalíticos eficientes y selectivos sigue siendo un desafío.
Los catalizadores a base de manganeso ofrecen una alternativa sostenible a los metales preciosos.

Objetivo del estudio:

Se informará de una silición deshidrogenativa catalizada por el manganeso (I) de alquenos terminales sin aditivos.
Identificar un precatalizador eficaz de manganeso para esta transformación.
Para aclarar el mecanismo de reacción y explorar el alcance del sustrato.

Principales métodos:

Se utilizó un complejo de alquilo-bisfosfina-manganeso ((I) estable en el banco, fac-[Mn ((dippe) ((CO) 3 ((CH2CH2CH3)), como precatalizador.
Investigó el proceso catalítico que involucra la inserción migratoria y la escisión del enlace Si-H.
Utilizó datos experimentales y cálculos de la Teoría Funcional de Densidad (DFT) para estudios mecanicistas.

Principales resultados:

El precatalizador convierte eficientemente una amplia gama de alquenos aromáticos y alifáticos.
Se logró la síntesis selectiva de E-vinilsilanos a partir de alquenos aromáticos y de alilsilanos a partir de alquenos alifáticos.
Se establecieron condiciones de reacción a temperatura ambiente, demostrando una alta eficiencia.

Conclusiones:

Se ha desarrollado con éxito una silición deshidrogenativa catalizada por Mn{I} de alquenos terminales sin aditivos.
La reacción procede a través de dos vías paralelas: una sin aceptor con liberación de dihidrógeno y otra que involucra al alqueno como aceptor de hidrógeno.
Esta metodología proporciona una vía versátil y eficiente para obtener compuestos orgánicos de silicio valiosos.