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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

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Enfoque sintético y predictivo de los bifenolos asimétricos por el acoplamiento oxidativo de radicales-aniones

Anna Libman¹, Hadas Shalit¹, Yulia Vainer¹

¹Department of Chemistry, Ben-Gurion University of the Negev , Beer-Sheva 84105, Israel.

Journal of the American Chemical Society

|August 20, 2015

Resumen

Un nuevo método catalizado por hierro permite el acoplamiento asimétrico de bifenol utilizando un mecanismo radical-anión. Este estudio presenta un modelo predictivo para la viabilidad del acoplamiento cruzado de fenol, avanzando la química orgánica sintética.

Área de la Ciencia:

Química orgánica
Catálisis
Mecanismo de reacción

Sus antecedentes:

La síntesis de bifenol es crucial en la química orgánica.
El desarrollo de métodos selectivos para el acoplamiento asimétrico de bifenol sigue siendo un desafío.

Objetivo del estudio:

Desarrollar un método de acoplamiento oxidativo catalizado por hierro para los bifenolos asimétricos.
Para aclarar el mecanismo de reacción y establecer un modelo predictivo para el acoplamiento cruzado.

Principales métodos:

Reacción de acoplamiento oxidativo catalizada por el hierro.
Estudios mecánicos, incluidos los métodos electroquímicos.
Cálculos de la teoría funcional de la densidad (DFT).

Principales resultados:

Desarrollo exitoso de un acoplamiento bifenólico asimétrico oxidativo catalizado por hierro.
La reacción se produce a través de un mecanismo de acoplamiento radical-anión quelado.
Se propuso un modelo general para predecir la viabilidad del acoplamiento cruzado para varios pares de fenol.

Conclusiones:

El método desarrollado ofrece una nueva vía para los bifenolos asimétricos.
Los conocimientos mecanicistas y el modelo predictivo facilitan el diseño racional de las reacciones de acoplamiento cruzado.
Este trabajo avanza en el campo de la formación catalítica de enlaces C-O.

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