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La activación del enlace carbono-carbono por la 1,1-carbororación de las alquinas internas

Chao Chen¹, Gerald Kehr, Roland Fröhlich

¹Organisch-Chemisches Institut, Universität Münster, Corrensstrasse 40, D-48149 Münster, Germany.

Journal of the American Chemical Society

|September 14, 2010

Resumen

Los alquinos internos reaccionan con boranos específicos en las reacciones de 1,1-carboboración, formando valiosos alquenilboranos trisubstituidos. Estos compuestos sirven como intermediarios clave en las reacciones de acoplamiento cruzado catalizadas por el paladio, expandiendo las posibilidades sintéticas.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Química orgánica sintética y orgánica.

Sus antecedentes:

Las alquinas internas son versátiles bloques de construcción en la síntesis orgánica.
Las reacciones de carboboración ofrecen métodos eficientes para la formación de enlaces carbono-boro.

Objetivo del estudio:

Para investigar la 1,1-carboboración de los alquinos internos utilizando nuevos reactivos de boro.
Para sintetizar alquenilboranos trisubstituidos y explorar su utilidad en reacciones posteriores.

Principales métodos:

Tratamiento de alcinos internos con boranos RB ((C ((6) F ((5)) 2) donde R = C ((6) F ((5) o CH ((3)).
Caracterización de los alquenilboranos trisubstituidos resultantes.
Aplicación de los alquenilboranos en reacciones de acoplamiento cruzado catalizadas por el paladio.

Principales resultados:

Se logró la exitosa 1,1-carboboración de los alquinos internos.
Los alquenilboranos trisubstituidos fueron sintetizados con alta eficiencia.
Los alquenilboranos sintetizados demostraron su utilidad como sustratos en reacciones de acoplamiento cruzado.

Conclusiones:

La metodología de carboboración desarrollada proporciona una nueva ruta a los alquenilboranos funcionalizados.
Este método ofrece una herramienta valiosa para la construcción de moléculas orgánicas complejas mediante acoplamiento cruzado.

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