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Síntesis directa de ésteres alquenil-borónicos a partir de alquenos no funcionalizados: una reacción de Boril-Heck

William B Reid¹, Jesse J Spillane¹, Sarah B Krause¹

¹Department of Chemistry and Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

Journal of the American Chemical Society

|April 23, 2016

Resumen

Este estudio introduce la primera reacción borilo-Heck utilizando un reactivo de boro electrófilo. El método catalizado por el paladio convierte los alquenos terminales en ésteres borónicos transalquenil eficientemente.

Área de la Ciencia:

Química organometálica
Síntesis orgánica
Catálisis

Sus antecedentes:

La reacción de Heck es una piedra angular de la formación de enlaces C-C.
Los ésteres de boro son productos intermedios sintéticos versátiles.
El desarrollo de nuevos métodos catalíticos para su síntesis es crucial.

Objetivo del estudio:

Para informar la primera reacción de borilo-Heck utilizando un reactivo de boro electrófilo.
Establecer un método catalizado por el paladio para la síntesis de ésteres borónicos transalquenílicos a partir de alquenos terminales.

Principales métodos:

Utilizó un catalizador de paladio para la reacción.
Se utiliza catecolcloroborane (catBCl) disponible en el mercado como fuente de boro.
Transesterificación realizada in situ para generar diversos aductos de boro.

Principales resultados:

Se ha logrado con éxito la conversión de alquenos terminales en ésteres borónicos transalquenílicos.
Demostró la utilidad del catecolchloroborane como un reactivo de boro electrófilo.
Se generan una variedad de ésteres borónicos, amidas y otros aductos de alquenilborón mediante transesterificación in situ.

Conclusiones:

Este trabajo presenta una nueva y eficiente reacción de borilo-Heck.
El método desarrollado ofrece una nueva vía para obtener compuestos valiosos de alquenil boro.
La versatilidad de la reacción permite amplias aplicaciones sintéticas.

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