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Acoplamiento C-C re-mediado de piridinas e imidazoles

Maialen Espinal Viguri¹, Miguel A Huertos, Julio Pérez

¹Departamento de Química Orgánica e Inorgánica-IUQOEM, Universidad de Oviedo-CSIC, C/Julián Clavería, 8, 33006 Oviedo-Spain.

Journal of the American Chemical Society

|December 5, 2012

Resumen

Los complejos de tricarbonilo de renio fueron modificados mediante desprotonación y oxidación. Este proceso creó nuevos ligandos bidentados a partir de precursores N-heterocíclicos, permitiendo nuevas reacciones de acoplamiento C-C y rearomatización.

Área de la Ciencia:

Química organometálica Química orgánica de los metales.
Coordinación Química de la Coordinación
Química sintética de la química sintética.

Sus antecedentes:

Los complejos de tricarbonilo de renio son precursores versátiles en la química organometálica.
Los ligandos N-heterocíclicos, como los N-alquilimidazoles y las piridinas, ofrecen diversas posibilidades de coordinación.
El desarrollo de nuevas rutas sintéticas para arquitecturas complejas de ligandos es crucial para el avance de la catálisis y la ciencia de los materiales.

Objetivo del estudio:

Investigar una nueva vía sintética para la generación de ligandos N-heterocíclicos bidentados.
Para explorar la desprotonación y el subsiguiente acoplamiento C-C de complejos tricarbonilo de renio que contienen ligandos N-heterocíclicos.
Para sintetizar y caracterizar nuevos complejos de renio con piridilimidazol o bipiridina ligandos bidentados.

Principales métodos:

Deprotonación de los complejos de tricarbonilo de renio mediante el uso de la amida de potasio bis (KN (SiMe3) 2).
Oxidación de los intermediarios desprotonados utilizando el triflato de plata (AgOTf).
Caracterización de los complejos de renio resultantes con piridilimidazol o bipiridina ligandos.

Principales resultados:

Deprotonación y oxidación exitosas de complejos de tricarbonilo de renio con ligandos N-heterocíclicos.
Formación de ligandos bidentados de piridilimidazol y bipiridina a través del acoplamiento C-C y la rearomatización.
Síntesis de nuevos complejos de renio que incorporan estos ligandos bidentados recién formados.

Conclusiones:

Se ha establecido una nueva estrategia sintética para acceder a los complejos de renio con los ligandos de piridilimidazol y bipyridine bidentate.
El método descrito permite la generación in situ y el acoplamiento de ligandos N-heterocíclicos.
Este trabajo amplía el alcance de la síntesis de ligandos en la química organometálica.

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