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Inestabilidad radical en ayuda de la eficiencia: una ruta poderosa hacia boronatos MIDA altamente funcionales
Béatrice Quiclet-Sire1, Samir Z Zard1
1Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
Journal of the American Chemical Society
|May 19, 2015
Resumen
Los boronatos de vinilo MIDA permiten una eficiente adición de xantato, creando estructuras funcionales de organoboron. Esta vía de reacción también permite el desplazamiento de xantato por bromo, facilitando nuevas transformaciones sintéticas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química del boro y su química.
Sus antecedentes:
- Los boronatos de MIDA son versátiles intermediarios sintéticos.
- La estabilización de los radicales adyacentes por el boro es un fenómeno conocido.
Objetivo del estudio:
- Para explorar la reactividad de los boronatos de vinilo MIDA con los xantatos.
- Desarrollar nuevos métodos para sintetizar compuestos de organoboron alifáticos funcionalizados.
Principales métodos:
- Reacción del boronato de vinilo MIDA con varios xantatos.
- Reacciones de adición radical.
- El desplazamiento de bromo de los adductos de xantato.
Principales resultados:
- Se logró una adición eficiente de diversos xantatos al boronato de vinilo MIDA.
- Formación de estructuras organoboronicas alifáticas altamente funcionalizadas.
- Intercambio exitoso de xantato con bromo, lo que permite una mayor derivación, incluida la síntesis de ciclopropano.
Conclusiones:
- La falta de estabilización radical por el boro sp(3) en los boronatos MIDA es clave para esta nueva reactividad.
- Este método proporciona acceso a diversos y funcionalizados compuestos de organoboron.
- La metodología desarrollada ofrece una nueva ruta para la síntesis de estructuras alifáticas complejas.
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