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Cianización reductora de haluros de arilo y derivados de fenol por transnitrilación

L Reginald Mills¹, Joshua M Graham¹, Purvish Patel¹

¹Davenport Research Laboratories, Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , ON M5S 3H6 , Canada.

Journal of the American Chemical Society

|November 12, 2019

Resumen

Este estudio introduce un nuevo método catalizado por níquel para la síntesis de benzonitriles utilizando un reactivo cianante seguro. El proceso produce eficientemente compuestos médicamente importantes y amplía el alcance del sustrato con bromuro de sodio.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los benzonitriles son un eje crucial en la química medicinal.
Los métodos existentes para la síntesis de benzonitrilo a menudo implican fuentes tóxicas de cianuro o condiciones adversas.

Objetivo del estudio:

Desarrollar un método nuevo, seguro y eficiente catalizado por níquel para la síntesis de benzonitrilo.
Para utilizar un reactivo cianante electrófilo estable en el banco, el 2-metil-2-fenil malononitrilo (MPMN).

Principales métodos:

Acoplamiento reductor catalizado por níquel de haluros de arilo (pseudo) con MPMN.
Optimización de las condiciones de reacción, incluido el uso de bromuro de sodio (NaBr) como aditivo.

Principales resultados:

Síntesis exitosa de varios benzonitriles médicamente relevantes en buenos rendimientos.
Utilidad demostrada del MPMN como fuente segura y eficaz de cianuro electrófilo.
Ampliación del ámbito de aplicación de los sustratos para incluir cloruros de arilo, tosilatos y triflados con la adición de NaBr.

Conclusiones:

El método desarrollado catalizado por Ni ofrece una vía práctica para los benzonitriles.
El MPMN ofrece una alternativa más segura a los reactivos de cianuro tradicionales.
El NaBr juega un papel clave en la activación de electrófilos de arilo menos reactivos, probablemente al facilitar la adición oxidativa.

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