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La diboración catalítica de aldehídos a través de la inserción en el enlace cobre-boro

David S Laitar¹, Emily Y Tsui, Joseph P Sadighi

¹Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.

Journal of the American Chemical Society

|August 24, 2006

Resumen

Este estudio detalla la primera inserción bien definida de un grupo carbonilo en un enlace metal-boro utilizando mesitaldehído y un complejo de cobre. Un nuevo precatalizador de cobre permite una eficiente 1,2-diboración de varios aldehídos.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis de la catálisis.
Química del boro y su química.

Sus antecedentes:

Los enlaces metal-boro son intermediarios cruciales en la síntesis orgánica.
Las reacciones de inserción de carbonilo son transformaciones fundamentales en la química.
El desarrollo de sistemas catalíticos eficientes para la formación de enlaces C-B es un área de investigación activa.

Objetivo del estudio:

Informar el primer producto bien definido de la inserción de un grupo carbonilo en un enlace cobre-boro.
Desarrollar un nuevo precatalizador de cobre para la eficiente 1,2-diboración de aldehídos.
Investigar el alcance y el mecanismo de esta nueva transformación.

Principales métodos:

Reacción del mesitaldehído con (IPr) CuB para formar el complejo 1.
Caracterización del complejo 1 utilizando espectroscopia de RMN y difracción de rayos X monocristalino.
Prueba catalítica de un precatalizador de cobre (I) con ligando ICy para la diboración del aldehído.

Principales resultados:

Se sintetizó y caracterizó el primer producto bien definido de la inserción de un grupo carbonilo en un enlace metal-boro.
Se confirmó la formación de un enlace cobre-carbono y un enlace boro-oxígeno.
Se logró una eficiente 1,2-diboración de aldehídos sustituidos por arilo, heteroarilo y alquilo a temperatura ambiente utilizando un precatalizador de cobre.

Conclusiones:

La inserción de un grupo carbonilo en un enlace cobre-boro es factible y produce un complejo estable y caracterizado.
Un nuevo sistema de precatalizador de cobre facilita la eficiente 1,2-diboración de una amplia gama de aldehídos.
Este trabajo amplía la utilidad sintética de los compuestos organoboron y la catálisis del cobre.

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