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Hidroxilación de substrato de nitrilo exógeno por un nuevo complejo de dicopro-hidroperoxido.

Lei Li¹, Amy A Narducci Sarjeant, Michael A Vance

¹Department of Chemistry, The Johns Hopkins University, Baltimore, MD 21218, USA.

Journal of the American Chemical Society

|November 3, 2005

Resumen

Un complejo de dicopro (I) reacciona con el oxígeno para formar una especie hidroperoxo. Este intermedio se somete a una transformación térmica, produciendo nitriles y cianuro hidroxilados, lo que demuestra la transferencia de átomos de oxígeno desde O2.

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Área de la Ciencia:

La química de la coordinación es química de la coordinación.
Química organometálica de las sustancias orgánicas.
Química bioorgánica y bioorgánica.

Sus antecedentes:

Los complejos de dicobre son modelos relevantes para las enzimas que contienen cobre.
Comprender la reactividad de los complejos de dicobre con el dioxígeno es crucial para la catálisis.
La funcionalización del nitrilo sigue siendo una transformación desafiante en la síntesis orgánica.

Objetivo del estudio:

Para investigar la reacción de un complejo de dicopro (I) / fenol-ligando con el dioxígeno.
Para aclarar el mecanismo de la hidroxilación del nitrilo y la eliminación del cianuro.
Para caracterizar los complejos de cobre resultantes y los productos orgánicos.

Principales métodos:

Reacción del complejo de dicopro (I) con O2 en disolventes de RCN.
Aislamiento y caracterización de los productos de reacción, incluido un grupo tetranuclear.
Etiquetado isotópico 18O para rastrear el origen del átomo de oxígeno.

Principales resultados:

Formación de una especie mu-1,1-hidroperoxo dicopper (II) en reacción con O2.
Transformación térmica que conduce a la hidroxilación del nitrilo y la liberación de cianuro.
Aislamiento de un grupo tetranuclear con puente de cianuro y benzaldehído (cuando R = PhCH2).
El etiquetado 18O confirmó que el oxígeno en el benzaldehído se origina en O2.

Conclusiones:

El complejo dicopro (I) /fenol-ligando activa el O2 para formar un intermediario hidroperoxo.
Este intermedio puede someterse a un reordenamiento térmico para lograr la hidroxilación del nitrilo.
El estudio proporciona información sobre las reacciones de oxigenación mediadas por cobre y los mecanismos de liberación de cianuro.