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Fusión de catálisis de NiH y transferencia de metal-nitrenoide de la esfera interna para la hidroamidación de

Xiang Lyu^1,2, Jianbo Zhang^1,2, Dongwook Kim^1,2

¹Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science, Daejeon 34141, South Korea.

Journal of the American Chemical Society

|April 9, 2021

Resumen

Este estudio introduce una nueva hidroamidación catalizada por hidróxido de níquel de alquinas utilizando dioxazolonas. Este método sintetiza eficientemente valiosas enamidas secundarias con selectividad controlable, superando las limitaciones anteriores en la funcionalización de alquinos.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La hidroaminación/hidroamidación catalizada por hidruro de metal es crucial para la síntesis de compuestos que contienen nitrógeno.
La hidroamidación directa de los alquinos es un desafío debido a las vías de reacción competitivas de los intermedios clave.

Objetivo del estudio:

Desarrollar una nueva estrategia catalítica para la hidroamidación directa de los alquinos.
Para lograr una selectividad controlada de (E) anti-Markovnikov o Markovnikov en la síntesis de la enamida.

Principales métodos:

Hidroamidación catalizada por hidróxido de níquel (NiH) de las alquinas con dioxazolonas.
Investigación de las condiciones de reacción, incluida la función del agua (H2O).

Principales resultados:

Síntesis exitosa de enamidas secundarias sintéticamente útiles tanto de las alquinas terminales como de las internas.
Se ha demostrado tolerancia a varios grupos funcionales.
Identificó el H2O como esencial para la alta rotación del catalizador y propuso un mecanismo de transferencia de nitrenoides en la esfera interna.

Conclusiones:

Este trabajo presenta el primer ejemplo de catálisis de Ni que permite la formación de metal-nitrenoides a partir de dioxazolonas para la hidroamidación de alquinos.
El método desarrollado ofrece una vía versátil para obtener valiosas enamidas con selectividad ajustable.

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