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Trifluorometil benzoato: un reactivo de trifluorometoksilación muy versátil
Min Zhou1, Chuanfa Ni1, Yuwen Zeng1
1Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Ling-Ling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|May 23, 2018
Resumen
Un nuevo reactivo, el trifluorometil benzoato (TFBz), permite reacciones de trifluorometoxilación eficientes. Se sintetiza fácilmente y demuestra una amplia utilidad sintética en diversas transformaciones orgánicas.
Área de la Ciencia:
- Química orgánica
- Química sintética
Sus antecedentes:
- La trifluorometoxilación es una transformación crucial en la química de medicamentos y materiales.
- El desarrollo de reactivos de trifluorometoxilación estables y accesibles sigue siendo un área activa de investigación.
Objetivo del estudio:
- Desarrollar un nuevo reactivo de trifluorometoxilación estable.
- Mostrar la versatilidad sintética del nuevo reactivo en diversas reacciones orgánicas.
Principales métodos:
- Síntesis de trifluorometil benzoato (TFBz) a partir de precursores de bajo costo mediante el uso de KF.
- Aplicación de TFBz en la trifluorometoxilación-halogenación de las arinas, la sustitución nucleofílica, el acoplamiento cruzado y la difuncionalización de alquenos.
Principales resultados:
- El trifluorometil benzoato (TFBz) se sintetizó con éxito y se demostró que era estable en el estante.
- El reactivo facilitó la trifluorometoksilación eficiente en varias reacciones, incluida una halogenación de trifluorometoksilación sin precedentes de arinas a temperatura ambiente.
- Se logró un acoplamiento cruzado exitoso con estananos de arilo y una difuncionalización asimétrica de alquenos.
Conclusiones:
- El trifluorometil benzoato (TFBz) es un reactivo valioso y versátil para la introducción del grupo trifluorometoxi.
- La facilidad de preparación y estabilidad del reactivo lo convierten en una alternativa atractiva para las reacciones de trifluorometoxilación.
- El desarrollo de TFBz amplía el conjunto de herramientas para los químicos sintéticos, particularmente en la síntesis de compuestos orgánicos fluorados.
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