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Hidroiminación catalizada por el níquel de las alcinas

Rajith S Manan¹, Praveen Kilaru¹, Pinjing Zhao¹

¹Department of Chemistry and Biochemistry, North Dakota State University, Fargo, North Dakota 58102, United States.

Journal of the American Chemical Society

|April 30, 2015

Resumen

Una nueva reacción catalizada por níquel sintetiza eficientemente los derivados de 2-aza-1,3-butadieno de los alquinos y las ketiminas. Este proceso de hidroiminación de eficiencia atómica produce exclusivamente estereoisómeros de (Z) -enamina.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

El desarrollo de rutas sintéticas eficientes para los heterociclos que contienen nitrógeno es crucial en la química orgánica.
Los derivados de 2-Aza-1,3-butadieno son bloques de construcción valiosos en la síntesis orgánica.

Objetivo del estudio:

Desarrollar una síntesis modular y de eficiencia atómica de los derivados de 2-aza-1,3-butadieno.
Para explorar una nueva reacción de acoplamiento intermolecular catalizada por níquel.

Principales métodos:

Acoplamiento intermolecular catalizado por níquel entre alquinas internas y ketiminas aromáticas N-H.
Utilizó un precursor de Ni ((0) ([Ni ((cod) 2), el ligando N-heterocíclico del carbeno (NHC) (IPr) y el aditivo Cs2CO3.
Sintetizó y caracterizó un complejo de Ni(0) π-imine ligado a NHC como precursor de un catalizador.

Principales resultados:

Logró una síntesis modular y de eficiencia atómica de los derivados de 2-aza-1,3-butadieno.
La reacción formó exclusivamente estereoisómeros de (Z) -enamina.
El complejo π-imine de Ni(0) sintetizado de forma independiente mostró una mayor reactividad catalítica.

Conclusiones:

Estableció un nuevo proceso de hidroiminación de alquino utilizando la catálisis del níquel.
El resultado estereoquímico apoya un mecanismo anti-minometalación.
El método desarrollado ofrece una vía eficiente a valiosos compuestos de enamina.

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