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Aprovechar las aminas alquilo como electrófilos para acoplamientos cruzados catalizados por níquel a través de la

Corey H Basch¹, Jennie Liao¹, Jianyu Xu¹

¹Department of Chemistry & Biochemistry, University of Delaware , Newark, Delaware 19716, United States.

Journal of the American Chemical Society

|April 1, 2017

Resumen

Los investigadores desarrollaron un nuevo método de acoplamiento cruzado Suzuki-Miyaura utilizando alquilaminas como agentes alquilantes a través de la activación de enlaces C-N. Esta nueva estrategia permite la instalación de grupos alquilo primarios y secundarios con un amplio alcance y tolerancia de grupo funcional.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las aminas alquilo son bloques de construcción cruciales en la síntesis orgánica.
La activación del enlace C-N en aminas para reacciones de acoplamiento cruzado sigue siendo un desafío significativo.
Los métodos existentes a menudo requieren grupos alquilo prefuncionalizados o condiciones duras.

Objetivo del estudio:

Desarrollar un nuevo método para utilizar las alquilaminas como agentes directos de alquilación.
Para lograr el acoplamiento cruzado catalizado por metal a través de la activación de enlaces C-N de aminas.
Ampliar el alcance y la tolerancia del grupo funcional en la alquilación basada en aminas.

Principales métodos:

Desarrollo de una reacción de acoplamiento cruzado Suzuki-Miyaura utilizando sales de alquilpiridinio derivadas de aminas primarias.
Investigación de las condiciones de reacción y de los sistemas catalizadores para la activación de enlaces C-N.
Exploración del alcance del sustrato que incluye varios grupos alquilo primarios y secundarios.

Principales resultados:

Se logró el primer ejemplo de acoplamiento cruzado catalizado por metal a través de la activación de un enlace C-N de una amina con un grupo alquilo no activado.
La reacción demostró un amplio alcance, acomodando diversos grupos alquilo primarios y secundarios.
Se observó una alta tolerancia del grupo funcional, lo que permite la presencia de varios sustituyentes.

Conclusiones:

Se ha establecido una estrategia versátil y eficiente para aprovechar las aminas alquilo como agentes alquilantes a través de la activación del enlace C-N.
Este método proporciona una nueva herramienta poderosa para la formación de enlaces C-C utilizando aminas fácilmente disponibles.
Los estudios mecanicistas preliminares sugieren un ciclo catalítico de níquel I / níquel III.

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