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Published on: May 21, 2019
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Oxidación de cloro y bromodifluorometilación de fenoles mediada por el cobre
Wen-Juan Yuan1, Chao-Lai Tong1, Xiu-Hua Xu1
1Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Science, 345 Lingling Lu, Shanghai 200032, China.
Journal of the American Chemical Society
|October 25, 2023
Resumen
Un nuevo método permite la síntesis de éteres de cloro- y bromodifluorometil-arilo mediante un proceso de difluorocarbeno. Este eficiente protocolo ofrece una ruta práctica a compuestos valiosos bajo condiciones suaves.
Área de la Ciencia:
- Química orgánica
- Química sintética
- Química medicinal
Sus antecedentes:
- Los difluorometil éteres de arilo son motivos estructurales importantes en los productos farmacéuticos y agroquímicos.
- Los métodos existentes para sintetizar estos compuestos a menudo requieren condiciones duras o reactivos especializados.
Objetivo del estudio:
- Desarrollar un método nuevo y eficiente para la metilación oxidativa de cloro y bromodifluoro de fenoles.
- Para sintetizar una amplia gama de cloro y bromodifluorometil éteres de arilo biológicamente valiosos.
Principales métodos:
- Se utilizan haluros de trimetilsililo (difluorometil) ((CH3) 3SiCF2X) y haluros de cobre (CuX) como reactivos.
- Utilizado Selectfluor como oxidante en condiciones de reacción suaves.
- Investigó el mecanismo de reacción a través de estudios preliminares.
Principales resultados:
- Se desarrolló con éxito la primera oxidación de cloro y bromodifluorometilación de fenoles.
- Se ha logrado una síntesis eficiente de varios éteres de cloro y bromodifluorometil arilo.
- Se identificó un proceso de acoplamiento oxidativo con difluorocarbenos como la vía de reacción probable.
Conclusiones:
- El protocolo desarrollado proporciona una vía sintética práctica y eficiente para los difluorometil éteres de arilo desafiantes.
- El método es aplicable a una amplia gama de fenoles, dando lugar a compuestos valiosos.
- Las ideas mecanicistas allanan el camino para un mayor desarrollo de estrategias de difluorometilación.
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