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Dirigir la hidrociliación controlada por grupo: funcionalización regioselectiva de la alquina

Yuuya Kawasaki¹, Youhei Ishikawa, Kazunobu Igawa

¹Department of Molecular and Material Sciences, Kyushu University, Kasuga, Fukuoka 816-8580, Japan.

Journal of the American Chemical Society

|December 7, 2011

Resumen

La hidrociliación catalizada por platino utilizando un grupo directivo de dimetilvinilsililo (DMVS) logra una alta regioselectividad para los alquinos asimétricos. Este método permite la síntesis de isómeros específicos de silílalqueno y diversos compuestos funcionalizados.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Química orgánica sintética y orgánica.
La catálisis es la catálisis.

Sus antecedentes:

La hidrosilación es una reacción clave en la síntesis orgánica.
El control de la regioselectividad en la hidrosilación de alquinos sigue siendo un desafío.
Los grupos de dirección pueden influir en los resultados de las reacciones.

Objetivo del estudio:

Desarrollar una hidrociliación altamente regioselectiva Pt(0)-catalizada de alquinas no simétricas.
Investigar el papel del grupo dimetilvinilsililo (DMVS) como grupo de dirección y aceleración.
Para explorar la síntesis de alquenos complejos y compuestos funcionalizados a partir de alquinos asimétricos.

Principales métodos:

Reacción de hidrociliación catalizada por el platino (((0)).
Utilizando el dimetilvinilsililo (DMVS) como grupo directivo en alquinos asimétricos.
Reacciones de transformación posteriores de los silílalquenos resultantes.

Principales resultados:

Se logra una alta regioselectividad en la hidrosilación de alquinas asimétricas.
El grupo DMVS dirigió la formación de un único regioisómero de los silílalquenos.
Se observó un efecto acelerador del grupo DMVS para la hidrosilación selectiva.
Sintetizó varios alquenos tri-sustituidos y compuestos multi-oxy-funcionalizados con alta regioselectividad.

Conclusiones:

El grupo DMVS es un grupo directivo y acelerador eficaz para la hidrociliación de alquinos catalizada por Pt(0).
Esta metodología proporciona una ruta regioselectiva para obtener valiosos derivados de alquenos.
Permite la síntesis eficiente de moléculas orgánicas complejas a partir de alquinas simples.

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