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Oxidación de aminas alifáticas catalizadas por platino y selectivas por C ((sp(3)) -H

Melissa Lee¹, Melanie S Sanford¹

¹Department of Chemistry, University of Michigan , 930 North University Avenue, Ann Arbor, Michigan 48109, United States.

Journal of the American Chemical Society

|October 7, 2015

Resumen

Este estudio presenta un nuevo método catalizado por platino para la oxidación de aminas alifáticas en la posición terminal. Este proceso eficiente evita la dirección de grupos y funciona para varios tipos de aminas.

Área de la Ciencia:

Química orgánica
Catálisis
Reacciones de oxidación

Sus antecedentes:

La oxidación directa C ((sp3) -H de aminas es difícil debido a la naturaleza coordinadora del átomo de nitrógeno.
Los métodos existentes a menudo requieren grupos dirigidos o condiciones duras.

Objetivo del estudio:

Desarrollar una oxidación terminal selectiva, catalizada por platino, de las aminas alifáticas.
Para lograr esta transformación sin la necesidad de dirigir grupos.

Principales métodos:

Utilizando el platino (Pt) como catalizador.
Utilizando el cloruro de cobre (CuCl2) como oxidante estequiométrico.
Realización de la reacción en presencia de ácido sulfúrico (H2SO4) para formar sales de amonio in situ.

Principales resultados:

Se obtienen altos rendimientos para la oxidación terminal selectiva C ((sp3) -H de aminas primarias, secundarias y terciarias.
Catalización efectiva con bajas cargas de platino (1 mol%).
El ácido sulfúrico desempeña múltiples funciones, incluida la solubilización del sustrato, la prevención del envenenamiento del catalizador y la desactivación electrónica de los enlaces C-H proximales.

Conclusiones:

El método desarrollado ofrece una vía eficiente y versátil para la oxidación terminal C ((sp3) -H de aminas alifáticas.
La protonación de aminas es una estrategia clave para permitir esta transformación catalítica selectiva.

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