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Carboheterofuncionalización oxidativa catalizada por oro homogéneo de los alquenos

Guozhu Zhang¹, Li Cui, Yanzhao Wang

¹Department of Chemistry and Biochemistry, University of California Santa Barbara, Santa Barbara, California 93106, USA.

Journal of the American Chemical Society

|January 7, 2010

Resumen

La catálisis del oro permite una síntesis eficiente de N- y O-heterociclos de alquenos a través de la carboaminación y reacciones relacionadas. Este estudio revela la anti-esteroquímica y el crucial ciclo catalítico Au (I) / Au (III), permitiendo nuevas formaciones de enlaces C-C.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
La catálisis por catálisis.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

La catálisis del oro ofrece una reactividad única para las transformaciones orgánicas.
El acceso a los N- y O-heterociclos sustituidos es crucial en la química medicinal.
La catálisis del oro oxidativo proporciona nuevas vías para la funcionalización.

Objetivo del estudio:

Desarrollar un método homogéneo catalizado por oro para la carboaminación, carboalcoxilación y carbolactonización de alquenos terminales.
Investigar el resultado estereoquímico y el mecanismo catalítico de las reacciones catalizadas por el oro.
Explorar la conversión de los intermediarios alquiloro en enlaces C-C a través del acoplamiento cruzado.

Principales métodos:

Catálisis del oro oxidativo utilizando alquenos terminales.
Estudios de etiquetado de deuterio para determinar el mecanismo de reacción y la estereoquímica.
Reacciones de acoplamiento cruzado que involucran intermediarios alquiloro.

Principales resultados:

Se logró una síntesis eficiente de diversos heterociclos N y O.
Anti-esteroquímica establecida de la funcionalización del alqueno.
Demostró la primera conversión catalítica de bonos C(sp3)-Au a bonos C(sp3)-C(sp2).

Conclusiones:

La catálisis del oro homogéneo proporciona una ruta versátil a los heterociclos.
El ciclo Au (I) / Au (III) es esencial para las transformaciones observadas.
Este trabajo abre nuevas vías para la funcionalización de alceno catalizado por oro y la formación de enlaces C-C.

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