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Borilación descarboxilada fotoinducida de los ácidos carboxílicos

Alexander Fawcett¹, Johan Pradeilles¹, Yahui Wang¹

¹School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.

Science (New York, N.Y.)

|June 17, 2017

Resumen

Este estudio introduce un nuevo método para la conversión de ácidos carboxílicos en ésteres de boro valiosos utilizando luz visible y un reactivo de diboro. Este avance ofrece una vía sintética versátil para varios compuestos orgánicos.

Área de la Ciencia:

Química orgánica
Metodología sintética
Fotocatálisis

Sus antecedentes:

Los ácidos carboxílicos son materiales de partida abundantes.
Los ésteres de boro son intermediarios sintéticos muy importantes.
Se necesitan métodos de conversión eficientes.

Objetivo del estudio:

Desarrollar un nuevo método para sintetizar ésteres de boro a partir de ácidos carboxílicos.
Para utilizar la fotocatálisis de luz visible para esta transformación.
Demostrar una amplia aplicabilidad y tolerancia del grupo funcional.

Principales métodos:

Activación de los ácidos carboxílicos a través de los ésteres de N-hidroxiftalimida.
Catalización por fotorreducción con luz visible.
Reacción con el reactivo bis (catécolato) diboro.
Aislamiento de ésteres borónicos de pinacol.

Principales resultados:

Conversión exitosa de ácidos alquilo carboxílicos primarios, secundarios y terciarios.
Utilidad demostrada con diversos ácidos carboxílicos de productos naturales.
La evidencia sugiere un mecanismo intermedio del radical borilo.
Se observó una alta tolerancia del grupo funcional.

Conclusiones:

Se ha establecido un método nuevo, eficiente y versátil para la síntesis de ésteres de boro a partir de ácidos carboxílicos.
La fotocatálisis con luz visible ofrece un enfoque sostenible.
La metodología muestra un potencial significativo para la síntesis de moléculas complejas.

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