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Borilación electroquímica de haluros de alquilo: Acceso rápido y escalable a los ésteres de alquilo boro
Bingbing Wang, Pan Peng, Wan Ma
1Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062, P. R. China.
Journal of the American Chemical Society
|August 10, 2021
Resumen
Un nuevo método de electrorreducción permite la borilación rápida, escalable y libre de metales de haluros de alquilo a ésteres de boro. Este proceso a temperatura ambiente es ampliamente aplicable, incluso para moléculas complejas.
Área de la Ciencia:
- Química orgánica
- La electroquímica
- Metodología sintética
Sus antecedentes:
- La borilación de haluros de alquilo es crucial para la síntesis de compuestos de organoboron.
- Los métodos existentes a menudo requieren metales de transición o condiciones duras.
Objetivo del estudio:
- Desarrollar una borilación electrorreductiva libre de metales de transición de haluros de alquilo.
- Proporcionar un método escalable y práctico para acceder a diversos ésteres de boro.
Principales métodos:
- Reducción electroquímica de haluros de alquilo (ioduros, bromuros y cloruros)
- Uso de bis (pinacolato) diboro (B2cat2) como reactivo y mediador.
- Condiciones de reacción a temperatura ambiente.
Principales resultados:
- Se ha logrado una borilación rápida y escalable de haluros de alquilo primarios, secundarios y terciarios.
- Se ha demostrado una amplia tolerancia del grupo funcional con más de 70 ejemplos.
- Aplicado con éxito a la borilación tardía de productos naturales y derivados farmacéuticos.
- Los estudios mecanicistas revelaron el doble papel de B2cat2 en la habilitación de la electroreducción de bajo potencial.
Conclusiones:
- El protocolo electrorreductivo desarrollado ofrece una ruta eficiente, sostenible y versátil para los ésteres de boro.
- Este método supera las limitaciones de las técnicas tradicionales de borilación.
- Tiene un potencial significativo para aplicaciones en química medicinal y ciencias de los materiales.
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