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Hidrogenación de nitrilo catalizada por cobalto y asistida por ácido de Lewis a aminas primarias: un esfuerzo

Kenan Tokmic¹, Bailey J Jackson¹, Andrea Salazar¹

¹School of Chemical Sciences, University of Illinois at Urbana-Champaign , 600 S. Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society

|September 15, 2017

Resumen

Este estudio presenta un catalizador de cobalto para la hidrogenación selectiva de nitriles a aminas primarias mediante el uso de gas hidrógeno. El subproducto del ácido de Lewis, el trietilborano (BEt3), es crucial para esta eficiente transformación química.

Área de la Ciencia:

Catálisis
Química orgánica
Química organometálica

Sus antecedentes:

La hidrogenación del nitrilo es una reacción clave para sintetizar aminas primarias.
El desarrollo de catalizadores eficientes y selectivos para esta transformación sigue siendo un objetivo importante en la síntesis orgánica.

Objetivo del estudio:

Informar sobre un nuevo precatalizador de cobalto estable para la hidrogenación selectiva de nitriles a aminas primarias.
Investigar el papel del subproducto del ácido de Lewis en el ciclo catalítico.

Principales métodos:

Hidrogenación selectiva de nitriles utilizando un precatalizador de cobalto bajo 4 atm de H2.
Reducción in situ del precursor del catalizador con trietilborohidruro de sodio (NaHBEt3).
Estudios mecánicos mediante la espectroscopia de transferencia de RMN por polarización inducida por parahidrógeno (PHIP).

Principales resultados:

El precatalizador de cobalto hidrogena efectivamente los nitriles en aminas primarias.
El ácido de Lewis, el trietilborano (BEt3), formado in situ, es esencial para la catálisis.
Los estudios PHIP-NMR indican que un proceso de redox Co (I/III) está involucrado en la hidrogenación en pares de los nitriles.

Conclusiones:

Se ha desarrollado un nuevo sistema catalítico para la hidrogenación de nitrilo.
El ácido de Lewis juega un papel integral en el mecanismo catalítico.
La reacción se lleva a cabo a través de una vía redox Co (I/III), proporcionando una visión mecánica de la hidrogenación del nitrilo.

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