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Ciclización intermolecular aeróbica catalizada por paládio/cobre de compuestos enediinos y alquinos: interrupción de

Fei Ling¹, Zexiang Li, Chenguang Zheng

¹Department of Chemistry, Zhejiang University , 20 Yugu Road, Hangzhou 310027, China.

Journal of the American Chemical Society

|July 26, 2014

Resumen

Una nueva reacción en tándem sintetiza de manera eficiente las isoindolinonas y los ácidos o-acilbenzoicos a partir de compuestos enediino-carboxílicos y alquinos utilizando catalizadores de paladio y cobre. Este método incorpora átomos de oxígeno de O2 y H2O en la estructura de enediyne.

Área de la Ciencia:

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

Sus antecedentes:

Los compuestos de enediyne son versátiles intermediarios sintéticos.
El desarrollo de métodos eficientes para la construcción de moléculas orgánicas complejas es crucial.
Las reacciones catalizadas por paladio son ampliamente utilizadas en la síntesis orgánica.

Objetivo del estudio:

Desarrollar una nueva reacción de acoplamiento-cetooxigenación en tándem.
Para sintetizar isoindolinonas y ácidos o-acilbenzoicos.
Para explorar la incorporación regioselectiva de los átomos de oxígeno.

Principales métodos:

Reacción de acoplamiento-cetooxigenación en tándem.
Utilizando un sistema catalítico PdCl2 / CuBr2.
Empleando una atmósfera de O2 y H2O.

Principales resultados:

Con éxito sintetizó isoindolinonas y ácidos o-acilbenzoicos.
Logró la incorporación regioselectiva de dos átomos de oxígeno en unidades de enediyne.
Demostró una estrategia formal de [4C + 2C] de bencanulación-dicetonía.

Conclusiones:

La reacción desarrollada proporciona una ruta eficiente a valiosos compuestos orgánicos.
El sistema catalítico y las condiciones de reacción permiten la incorporación precisa de oxígeno.
Este trabajo amplía la utilidad sintética de las enediinas y las alquinas.

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