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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Hidrosilación regiodivergente y enantioselectiva de allenos catalizados por cobre

Jian-Lin Xu¹, Zhe-Yuan Xu¹, Zi-Lu Wang¹

¹Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. China.

Journal of the American Chemical Society

|March 17, 2022

Resumen

La catálisis del cobre permite la hidrociliación regiodivergente de los allenos, produciendo alilisilanos lineales y ramificados. Se logró una alta enantioselectividad para los alilsilanos ramificados utilizando un nuevo ligando de bisfosfina.

Área de la Ciencia:

Química organometálica
Catálisis
Química orgánica sintética

Sus antecedentes:

La hidrosilación es una reacción clave para la formación de enlaces carbono-silicio.
El control de la regioselectividad y la enantioselectividad en la hidrociliación del aleno sigue siendo un desafío.

Objetivo del estudio:

Desarrollar una hidrociliación regiodivergente catalizada por el cobre de alenos simples.
Para lograr una alta enantioselectividad en la hidrociliación asimétrica de los allenos.

Principales métodos:

Reacción catalizada por el cobre utilizando varios allenes.
Selección con disolventes para controlar la regioselectividad.
El uso de un ligando de bisfosfina C2-simétrico para la catálisis asimétrica.

Principales resultados:

Se logró la hidrosilación regiodivergente de una amplia gama de alenos.
Los alilisilanos lineales y ramificados se formaron selectivamente mediante la elección del disolvente.
Se obtuvieron alilisilanos ramificados con un exceso enantiomérico de hasta el 97%.

Conclusiones:

Se establece un método versátil catalizado por cobre para la hidrociliación de alenos.
El protocolo desarrollado permite la síntesis sintonizable de alilsilanos con regioquímica controlada.
La catálisis asimétrica proporciona acceso a los alilsilanos enriquecidos enantioméricamente.

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