Video Experimental Relacionado

Updated: Sep 9, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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Published on: January 19, 2016

Oxidación con cloro y bromodifluorometilación de los tiofenoles

Yu-Sheng Zhou¹, Wen-Juan Yuan¹, Jia-Yi Shou¹

¹State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

Organic letters

|August 29, 2025

Resumen

Este estudio introduce un método sin metales para la síntesis de sulfuros de cloro y bromodifluorometil arilo a partir de tiofenoles. El protocolo eficiente utiliza reactivos fácilmente disponibles bajo condiciones suaves, ofreciendo una ruta práctica a compuestos valiosos.

Área de la Ciencia:

Química orgánica
Química sintética
Química del fluor

Sus antecedentes:

Los compuestos difluorometilados son cruciales en productos farmacéuticos y agroquímicos.
Los métodos eficientes para la introducción de grupos difluorometílicos son muy buscados.
Los métodos existentes a menudo requieren condiciones duras o reactivos especializados.

Objetivo del estudio:

Desarrollar un nuevo método sin metales para la metilación de cloro y bromodifluoro.
Para sintetizar sulfuros de cloro y bromodifluorometilo de valor biológico.
Para establecer un protocolo sintético práctico y eficiente.

Principales métodos:

Oxidación por cloro y bromodifluorometilación de los tiofenoles.
Utilizó el difluorometil trimetilsilido (TMSCF2X) como fuente de difluorometil.
Utiliza N-cloro (bromo) succinimida como oxidante y haluro de tetrabutilamonio (nBu4NX) como fuente de haluro.

Principales resultados:

Se han sintetizado con éxito varios sulfuros de cloro y bromodifluorometil arilo.
Logró la transformación bajo condiciones de reacción suaves.
Demostró un protocolo práctico y eficiente para la síntesis de difluorometil sulfuro.

Conclusiones:

El protocolo desarrollado ofrece una ruta eficiente libre de metales para los valiosos sulfuros de arilo difluorometilados.
El método es práctico para sintetizar compuestos diversos y desafiantes.
Los estudios mecánicos sugieren la participación de un intermediario difluorocarbeno.

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