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Ruthenium(0) Endiyne-α-Ketol catalizado [4 + 2] Cicloadición: ensamblaje convergente de subestructuras policetidas de

Aakarsh Saxena¹, Felix Perez¹, Michael J Krische¹

¹University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, United States.

Journal of the American Chemical Society

|May 5, 2015

Resumen

Los catalizadores de rutenio permiten una nueva reacción entre las benzo-eninas y las alfa-cetol, formando complejas estructuras policetídicas a través de la cicloadición. Este método ofrece un enfoque convergente para la síntesis de valiosos compuestos químicos.

Área de la Ciencia:

Química orgánica es la química orgánica.
La catálisis de la catálisis.
Metodología sintética de la metodología sintética.

Sus antecedentes:

Las 1,5-diinas (benzoeninas) 3,4-benzanuladas son versátiles bloques de construcción en la síntesis orgánica.
Los cetoles alfa (alfa-hidroxicetonas) son importantes grupos funcionales con una reactividad diversa.
Los catalizadores de rutenio se emplean ampliamente para diversas transformaciones orgánicas, incluidas las cicloadiciones y las reacciones de acoplamiento.

Objetivo del estudio:

Desarrollar un nuevo método catalítico para la síntesis de subestructuras de policetídeos.
Para investigar la reacción entre las benzo-eninas y los alfa-cetolos mediada por catalizadores de rutenio.
Para aclarar el mecanismo de la observada [4+2] cicloadición.

Principales métodos:

Utilizados catalizadores Ru(0) generados in situ a partir de Ru3(CO) 12 con ligandos de fosfina (RuPhos o CyJohnPhos).
Reaccionaron las benzo-eninas con varios alfa-cetolos bajo condiciones catalíticas.
Productos de reacción caracterizados mediante el uso de técnicas espectroscópicas (por ejemplo, RMN, espectrometría de masas).

Principales resultados:

Se logró el acoplamiento C-C sucesivos desencadenados por redox entre benzo-eninas y alfa-cetolos.
Productos generados con éxito de [4+2] cicloadición.
Propuso un mecanismo catalítico que involucra acoplamientos oxidativos consecutivos alquino-carbonilo y hidrogenolización de transferencia.

Conclusiones:

Desarrolló una nueva ruta sintética convergente para las subestructuras poliquetídicas de tipo II.
Demostró la utilidad de los catalizadores Ru(0) en la mediación de reacciones complejas de cicloadición.
La reacción ofrece una poderosa herramienta para ensamblar intrincadas arquitecturas moleculares.

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