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Acoplamiento conjuntivo catalizado por Pd entre complejos de boro "Ate" derivados de Grignard y haluros o trilatos:

Gabriel J Lovinger¹, Mark D Aparece¹, James P Morken¹

¹Department of Chemistry, Merkert Chemistry Center, Boston College , Chestnut Hill, Massachusetts 02467, United States.

Journal of the American Chemical Society

|February 7, 2017

Resumen

Este estudio introduce un método eficiente para crear ésteres organobóricos quirales utilizando reactivos de Grignard en acoplamientos cruzados conjuntivos enantioselectivos catalíticos. El triflato de sodio juega un papel clave en la activación de la reacción y la prevención de la inhibición del catalizador.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los reactivos de Grignard son compuestos organometálicos versátiles.
La síntesis enantioselectiva es crucial para los productos farmacéuticos.
Los ésteres organobóricos son valiosos intermediarios sintéticos.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento cruzado conjuntivo catalítico enantioselectivo.
Para utilizar reactivos de Grignard en esta transformación.
Para sintetizar los ésteres organobóricos quirales no racémicos de manera eficiente.

Principales métodos:

El uso de reactivos de Grignard en acoplamientos cruzados conjuntivos enantioselectivos catalíticos.
Utilizando el triflato de sodio como un aditivo clave.
Optimización de las condiciones de reacción para la eficiencia y la selectividad.

Principales resultados:

Síntesis exitosa de varios ésteres organobóricos quirales no racémicos.
Se obtuvieron altos rendimientos y una excelente enantioselectividad.
Se demostró la doble función del triflato de sodio en la facilitación de la reacción.

Conclusiones:

El método desarrollado proporciona una ruta eficiente a los ésteres organobóricos quirales.
El trilato de sodio es esencial para superar desafíos como la formación de complejos de "comer" y la inhibición de haluros.
Esta metodología amplía el conjunto de herramientas para la síntesis asimétrica.

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