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Updated: Jun 11, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Procesos relacionados con la C-H trifluorometiolación propargílica enantioselectiva catalizada por iridio

Jiao Yu¹, Yue Xia¹, Shalini Dey¹

¹Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15213, United States.

Journal of the American Chemical Society

|October 1, 2024

Resumen

Los investigadores desarrollaron un nuevo método catalizado por iridio para la trifluorometiolación enantioselectiva de alquinas. Este enfoque proporciona acceso a valiosos tioéteres de trifluorometil y compuestos relacionados con una alta estereoselectividad.

Área de la Ciencia:

Química orgánica
Química medicinal
Catálisis

Sus antecedentes:

El grupo trifluorometiltio (SCF3) es cada vez más importante en el diseño de fármacos debido a sus propiedades únicas.
La síntesis de compuestos que contienen SCF3 enantioméricamente puros sigue siendo un desafío significativo.

Objetivo del estudio:

Desarrollar un método enantioselectivo para la introducción del grupo trifluorometiltio en los derivados de alquina.
Ampliar el acceso sintético a los compuestos fluoroorgánicos enriquecidos con enantio.

Principales métodos:

La trifluorometiolación enantioselectiva catalizada por iridio de los enlaces propargílicos C ((sp3) -H en las alquinas.
Se han utilizado diversos sustratos alquinos, incluidos los alquinos terminales protegidos y los de productos naturales/farmacéuticos.

Principales resultados:

Se obtienen rendimientos de buenos a excelentes y estereoselectividad para los tioéteres de trifluorometil.
Se ha demostrado el alcance del sustrato en varios tipos de alquinos.
Se modificó con éxito el protocolo para la síntesis de difluorometilo (SCF2H) y clorodifluorometilo (SCF2Cl).

Conclusiones:

El protocolo desarrollado ofrece una vía eficiente para los tioéteres de trifluorometilo enriquecidos con enantio.
Este método amplía significativamente el alcance de las moléculas fluoroorgánicas enriquecidas con enantio accesibles para el descubrimiento de fármacos.

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