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Grupo de dirección en el acoplamiento cruzado descarboxilativo: formación de enlaces C-N selectivos en el sitio

Zhao-Jing Liu¹, Xi Lu¹, Guan Wang¹

¹Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, University of Science and Technology of China , Hefei 230026, China.

Journal of the American Chemical Society

|July 21, 2016

Resumen

La catálisis del cobre permite la aminación descarboxilada dirigida de los ácidos carboxílicos alifáticos. Este método sintetiza de manera eficiente los derivados de pirrolidina y piperidina y modifica los productos naturales con una alta selectividad del sitio.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Los ácidos carboxílicos son bloques de construcción abundantes y versátiles.
El desarrollo de estrategias eficientes de formación de enlaces C-N es crucial en la síntesis orgánica.
La funcionalización dirigida ofrece un mayor control sobre las reacciones químicas.

Objetivo del estudio:

Desarrollar una reacción de aminación descarboxilada dirigida catalizada por cobre.
Para permitir la síntesis de heterociclos que contienen nitrógeno.
Proporcionar un método para modificar moléculas complejas.

Principales métodos:

Utilizando un catalizador de cobre para la aminación descarboxilada.
Emplear una estrategia de grupo de dirección para la selectividad del sitio.
Aplicando la reacción a los ácidos carboxílicos alifáticos no activados.

Principales resultados:

Síntesis eficiente de los derivados de pirrolidina y piperidina.
Modificación exitosa de productos naturales complejos.
Se ha demostrado una excelente selectividad del sitio en la formación de enlaces C-N.

Conclusiones:

El método desarrollado ofrece una ruta novedosa para la formación de enlaces C-N.
Este trabajo avanza en las reacciones de acoplamiento cruzado descarboxilador de radicales controlables.
La estrategia proporciona acceso a valiosos compuestos heterocíclicos.

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