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Acoplamiento descarbonilativo catalizado por Rh con alquinas a través de la activación C-C de las isatinas

Rong Zeng¹, Guangbin Dong

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

Journal of the American Chemical Society

|January 9, 2015

Resumen

Este estudio introduce una nueva reacción de acoplamiento descarbonilativo catalítico entre isatinas y alquinas. Este método sintetiza eficientemente los derivados de 2-quinolinona con alta regioselectividad.

Área de la Ciencia:

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

Sus antecedentes:

Las isatinas son compuestos heterocíclicos versátiles.
El desarrollo de rutas sintéticas eficientes para los derivados de 2-quinolinona es de gran interés.

Objetivo del estudio:

Para reportar una nueva [5 + 2 - 1] transformación para sintetizar derivados de 2-quinolinona.
Para explorar el acoplamiento descarbonilativo catalítico entre isatinas y alquinas.

Principales métodos:

Utilizando una reacción de acoplamiento descarbonilativo catalítico.
Empleando isatinas y una amplia gama de alquinas.
Investigando el papel de los grupos de dirección (DG).

Principales resultados:

Se han sintetizado con éxito derivados de la 2-quinolinona.
Se logró un acoplamiento eficiente con una alta regioselectividad.
Se ha demostrado la activación C-C de las isatinas a temperatura ambiente, facilitada por la DG.

Conclusiones:

El acoplamiento descarbonilativo catalítico desarrollado ofrece una vía única y eficiente a los derivados de 2-quinolinona.
El mecanismo de reacción implica la activación de C-C, la descarbonización y la inserción de alquinos, con grupos de dirección que juegan un papel crucial.

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