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Expansión del anillo de los boronatos cíclicos a través de la oxiboración de las arinas
Yuma Shiratori1, Julong Jiang2, Koji Kubota1,3
1Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.
Journal of the American Chemical Society
|January 10, 2024
Resumen
Los investigadores lograron la primera oxiboración de arinas, creando nuevos ésteres de ácido borínico de siete miembros con anillo expandido. Esta reacción ofrece una nueva vía para sintetizar compuestos orgánicos complejos.
Área de la Ciencia:
- Química orgánica
- Química del organoboron
Sus antecedentes:
- Las arinas son intermedios altamente reactivos cruciales en la síntesis orgánica.
- El desarrollo de nuevos métodos para la funcionalización de aryne sigue siendo un área de investigación activa.
Objetivo del estudio:
- Para lograr la primera oxidación de arinas.
- Para sintetizar nuevos ésteres de ácido borínico de siete miembros con anillo expandido.
Principales métodos:
- Reacción de los derivados del 2-arilo-1,3,2-dioxaborolano con los precursores del aryno.
- Se utiliza fluoruro de cesio (CsF) como catalizador.
- Se emplearon estudios mecanicistas experimentales y cálculos de la teoría funcional de la densidad (DFT).
Principales resultados:
- Demostró con éxito la primera oxiboración de arinas.
- Sintetizó una serie de ésteres de ácido borínico de siete miembros con anillo expandido.
- Identificó la activación selectiva del enlace boro-oxígeno como el paso clave.
Conclusiones:
- El método desarrollado proporciona una nueva vía para la oxiboración de aryne.
- El mecanismo de reacción implica la formación de complejos de boro y la posterior inserción de aryne.
- Este trabajo expande la utilidad sintética de las arinas y los compuestos de organoboron.
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