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Hidroaminación selectiva proximal catalizada por NiH de alquenos no activados

Jinwon Jeon^1,2, Changseok Lee^1,2, Huiyeong Seo^1,2

¹Department of Chemistry, Korea Advanced Institute of Science and Technology, Daejeon 34141, Korea.

Journal of the American Chemical Society

|November 18, 2020

Resumen

Este estudio introduce un nuevo sistema catalizado por hidróxido de níquel para la hidroaminación regioselectiva de alquenos no activados utilizando diversas aminas. Este método sintetiza de manera eficiente bloques de construcción valiosos de aminoácidos y permite la funcionalización en etapa tardía de moléculas complejas.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

La hidroaminación de alquenos no activados sigue siendo un desafío importante en la síntesis orgánica.
El desarrollo de métodos regioselectivos para la instalación de aminas es crucial para acceder a valiosos andamios químicos.

Objetivo del estudio:

Desarrollar un sistema modular catalizado por hidróxido de níquel para la hidroaminación selectiva proximal de alquenos no activados.
Para permitir la síntesis de diversos bloques de construcción de aminoácidos β y γ y facilitar la funcionalización en etapa tardía.

Principales métodos:

Se utilizó un sistema catalizado por níquel-hidruro (NiH) con un grupo de dirección bidentado para promover la inserción de NiH en las olefinas.
Condiciones de reacción optimizadas para la hidroaminación regioselectiva de alquenos no activados terminales y internos.
Se empleó una combinación de estudios experimentales y computacionales para dilucidar el mecanismo de reacción.

Principales resultados:

Se ha logrado la hidroaminación selectiva proximal de una amplia gama de alquenos no activados con aminas primarias y secundarias.
Demostró un excelente control de la región en la instalación de grupos de aminas.
Aplicó con éxito el protocolo para la modificación en etapa tardía de moléculas complejas y médicamente relevantes.

Conclusiones:

El sistema catalizado por NiH desarrollado ofrece un enfoque flexible y general para sintetizar valiosos derivados de aminoácidos.
La metodología proporciona una herramienta poderosa para la funcionalización regioselectiva de alquenos y la modificación en etapa tardía de estructuras complejas.
El estudio proporciona información mecanicista sobre el proceso de hidroaminación catalizado por níquel.

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