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F^- Alquilación inducida por adición nucleofílica

Panpan Tian^1,2, Cheng-Qiang Wang¹, Sai-Hu Cai^1,2

¹Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University , 30 South Puzhu Road, Nanjing 211816, P. R. China.

Journal of the American Chemical Society

|December 15, 2016

Resumen

Este estudio introduce un nuevo método catalizado por el paladio para la alilación utilizando la iniciación con fluoruro. Crea eficientemente compuestos trifluorometilados, superando los desafíos sintéticos anteriores.

Área de la Ciencia:

Química orgánica
Química del fluor
Catálisis

Sus antecedentes:

Los grupos trifluorometilo son importantes en productos farmacéuticos y materiales.
La generación de carbaniones trifluorometílicos para las reacciones es un desafío.
Los métodos de alilación existentes tienen limitaciones para los compuestos trifluorometílicos.

Objetivo del estudio:

Desarrollar una nueva estrategia para la síntesis de derivados del homoaliltrifluorometano.
Para permitir la alilación formal de los derivados del trifluoroetileno.
Para superar las limitaciones en la alilación deprotonativa de los compuestos trifluorometil.

Principales métodos:

La alquilación alilica catalizada por el paladio.
Adición nucleofílica de fluoruro externo a las gemas difluoroalquenas.
Generación in situ de beta-trifluorocarbaniones

Principales resultados:

Síntesis exitosa de varios derivados del trifluorometano.
Se ha demostrado una gran modularidad y simplicidad operativa.
Amplio alcance del sustrato para los carbonatos de alilo y los derivados del trifluoroetileno.

Conclusiones:

El nuevo protocolo proporciona una ruta eficiente a los valiosos compuestos metilados por trifluoro.
Este método amplía las posibilidades sintéticas en la química del organofluoro.
La estrategia ofrece una alternativa práctica para acceder a moléculas complejas.

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