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Acoplamiento transversal descarboxilador de ésteres de N-hidroxiftalimida con yoduros de arilo

Kierra M M Huihui¹, Jill A Caputo¹, Zulema Melchor¹

¹Department of Chemistry, University of Rochester , Rochester, New York 14627-0216, United States.

Journal of the American Chemical Society

|April 1, 2016

Resumen

Un nuevo método catalizado por níquel permite el acoplamiento descarboxilativo de ésteres de N-hidroxiftalimida (NHP) con yoduros de arilo sin luz ni fotocatalizadores. Esta reacción eficiente forma arenas alquiladas de varios grupos alquilo, incluidos el metilo, primario y secundario.

Área de la Ciencia:

Química orgánica
Catálisis
Metodología sintética

Sus antecedentes:

Las reacciones de acoplamiento descarboxilativo son cruciales para la formación de enlaces C-C.
Los métodos anteriores a menudo se basan en fotocatalizadores, luz o precursores específicos.
El desarrollo de acoplamientos descarboxiladores catalizados por metales ofrece rutas sintéticas alternativas.

Objetivo del estudio:

Presentar un nuevo método de acoplamiento descarboxilativo catalizado por níquel.
Para permitir el acoplamiento de ésteres de N-hidroxiftalimida (NHP) con yoduros de arilo.
Establecer una vía mediada por metales distinta de los enfoques basados en radicales.

Principales métodos:

Utilizando níquel como catalizador y zinc como agente reductor.
El uso de ésteres de N-hidroxiftalimida de alquilo (NHP) como agentes de alquilación.
Reaccionan los ésteres de NHP con los yoduros de arilo en condiciones optimizadas.

Principales resultados:

Se ha logrado un acoplamiento descarboxilativo eficiente de ésteres de NHP alquilo metilo, primarios y secundarios con yoduros de arilo.
Se obtienen buenos rendimientos medios (77%) para las arenas alquiladas.
Se ha demostrado la reacción directa de complejos de arilníquel (II) con ésteres de NHP, formando arenas alquiladas.

Conclusiones:

El método desarrollado catalizado por níquel proporciona una vía práctica para sintetizar arenas alquiladas.
Este enfoque evita la necesidad de fotocatalizadores, luz o reactivos arilmetálicos.
El estudio pone de relieve la participación directa de los intermediarios de arilníquel (II) en el proceso de alquilación.

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