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Observación directa de la inserción de aldehído en los complejos rodio-arilo y -alcóxido

Christopher Krug¹, John F Hartwig

¹Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.

Journal of the American Chemical Society

|February 21, 2002

Resumen

Los complejos de organoorodio (I) reaccionan con aldehídos de arilo, dando cetonas en condiciones no acuosas y diarilmetanolos en mezclas acuosas. Los estudios mecánicos revelan la inserción de aldehído en el enlace rodio-arilo como el paso clave.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Catalización con el rodio.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los complejos de Organorhodium (I) ofrecen una reactividad única para las transformaciones orgánicas.
La comprensión de los mecanismos de reacción es crucial para el desarrollo de metodologías sintéticas eficientes.

Objetivo del estudio:

Para investigar la reactividad de los complejos de organorhodio (I) con aldehídos de arilo.
Para dilucidar el mecanismo de la formación de cetona y diarilmetanol.
Para explorar la síntesis de ésteres a través de una vía de doble inserción.

Principales métodos:

Síntesis y aislamiento de los complejos de organorhodium.
Reacción de complejos con aldehídos de arilo bajo diferentes condiciones de disolvente (THF no acuoso y acuoso).
Estudios mecánicos que incluyen efectos de isótopos cinéticos y caracterización intermedia.

Principales resultados:

Las cetonas se forman en buen rendimiento en condiciones no acuosas a través de la inserción de aldehído y la eliminación de beta-hidruro.
Los diarilmetanolos se generan exclusivamente en mezclas THF/agua a través de la inserción de aldehídos y la hidrólisis.
Se observó y caracterizó directamente un intermediario de diarilmetóxido de rodio.
Los ésteres se forman a través de una doble inserción y una secuencia de eliminación de beta-hidrógeno con el exceso de aldehído.

Conclusiones:

La vía de reacción está dictada por las condiciones del disolvente, lo que lleva a cetonas o diarilmetanolos.
La inserción de aldehído en el enlace rodio-arilo es el paso principal.
Las reacciones intermedias y posteriores observadas apoyan un mecanismo que implica la eliminación y/o hidrólisis de beta-hidrógeno.

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