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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

La trifluorometilación oxidativa aeróbica mediada por cobre de las alquinas terminales con Me3SiCF3

Lingling Chu¹, Feng-Ling Qing

¹Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

Journal of the American Chemical Society

|May 11, 2010

Resumen

Una nueva reacción catalizada por cobre agrega de manera eficiente grupos trifluorometilo a las alquinas terminales utilizando un reactivo fácilmente disponible. Este método es versátil, tolerando varios grupos funcionales para la síntesis de acetileno trifluorometilado.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química organometálica Química orgánica de los metales.

Sus antecedentes:

Los compuestos trifluorometilados son cruciales en los productos farmacéuticos y la ciencia de los materiales.
Es muy deseable desarrollar métodos eficientes para introducir el grupo trifluorometilo.

Objetivo del estudio:

Desarrollar una eficiente trifluorometilación mediada por cobre de las alquinas terminales.
Establecer un método general y práctico para la síntesis de acetileno trifluorometilado.

Principales métodos:

Reacción mediada por el cobre utilizando un reactivo nucleófilo trifluorometilador, el trimetil (trifluorometil) silano (Me3SiCF3).
Utilizó alquinas terminales aromáticas y alifáticas como sustratos.

Principales resultados:

Se logró con éxito una trifluorometilación eficiente de las alquinas terminales.
Tolerancia demostrada a diversos grupos funcionales incluyendo amino, -OMe, -CO2Et, -Br y -NO2.
Se obtienen acetilenos trifluorometilados con altos rendimientos y pureza.

Conclusiones:

La reacción mediada por cobre desarrollada es un método general, sencillo y prácticamente útil.
Este protocolo ofrece una herramienta valiosa para la síntesis de acetileno trifluorometilado.

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