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Acoplamiento oxidativo catalizado por bismuto de ácidos arilborónicos con sales triflatas y nonaflatas

Oriol Planas¹, Vytautas Peciukenas¹, Josep Cornella¹

¹Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, Mülheim an der Ruhr, 45470, Germany.

Journal of the American Chemical Society

|June 16, 2020

Resumen

Este estudio introduce una nueva reacción de acoplamiento cruzado catalizada por bismuto. Forma eficientemente enlaces carbono-oxígeno utilizando ácidos arilborónicos y sales de perfluoroalquilo sulfonato, habilitados por un ciclo redox Bi (III) / Bi (V).

Área de la Ciencia:

Química orgánica
Química organometálica

Sus antecedentes:

Las reacciones de acoplamiento son fundamentales en la síntesis orgánica.
El desarrollo de nuevos sistemas catalíticos para la formación de enlaces CO sigue siendo un desafío importante.

Objetivo del estudio:

Desarrollar un nuevo protocolo de acoplamiento cruzado bicatalizado para la formación de enlaces C ((sp2) -O.
Para utilizar las sales de perfluoroalquilo sulfonato fácilmente disponibles como socios de acoplamiento.

Principales métodos:

Reacción de acoplamiento cruzado catalizada por bismuto.
Utilizando un ligando de sulfones con deficiencia de electrones.
Utilizando ácidos arilborónicos y sales de perfluoroalquilo sulfonato (NaOTf, KONf).
Investigar el mecanismo de reacción mediante estudios preliminares y cálculos teóricos.

Principales resultados:

Construcción exitosa de los enlaces C ((sp2) -O.
Demostración de un ciclo redox de Bi (III) y Bi (V).
Identificación de un intermediario Bi ((V) altamente electrófilo.
Rápida eliminación del triflato de fenilo.

Conclusiones:

El protocolo desarrollado ofrece un método eficiente para la formación de enlaces C(sp2) -O.
El mecanismo de reacción involucra a una especie electrofílica clave Bi ((V).
Este trabajo expande el alcance de las reacciones catalizadas por bismuto y la construcción de enlaces C-O.

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