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El difluorocarburo de cobre permite la difluorometilación catalítica

Xin Zeng¹, Jimin Yang¹, Wei Deng¹

¹Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials (Chinese Academy of Sciences), Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Journal of the American Chemical Society

|June 7, 2024

Resumen

Una nueva reacción catalizada por cobre permite la difluorometilación de varias moléculas orgánicas utilizando una fuente de difluorocarbeno de bajo costo. Este método eficiente ofrece una alta selectividad y tolerancia del grupo funcional, creando valiosos compuestos fluorados.

Área de la Ciencia:

Química orgánica
Química sintética
Catálisis

Sus antecedentes:

El difluorocarbeno es un reactivo versátil en la síntesis orgánica.
Su alta reactividad limita su aplicación generalizada.
Se necesitan nuevos métodos para la difluorometilación controlada.

Objetivo del estudio:

Para desarrollar una nueva reacción de difluorometilación catalizada por cobre.
Para utilizar un precursor de difluorocarbeno de bajo costo.
Para lograr una difluorometilación eficiente y selectiva de varios sustratos.

Principales métodos:

Reacción de acoplamiento catalizada por cobre.
Se utiliza cianoborohidruro de sodio (NaBH3CN) y acetato de potasio (bromodifluoro) (BrCF2CO2K) como precursor del difluorocarbeno.
Los electrófilos de alilo y propargilo empleados.

Principales resultados:

Se ha logrado la difluorometilación de diversos electrofilos de alilo/propargilo.
Se ha demostrado una alta rentabilidad, estereoselectividad y regioselectividad.
Demostró una alta tolerancia funcional del grupo, incluso en moléculas complejas similares a fármacos.
Compuestos difluorometilados deuterados de interés medicinal.

Conclusiones:

El método desarrollado representa un nuevo modo de difluorometilación.
La formación intermedia del difluorocarburo de cobre es crucial.
Los productos resultantes son sintones versátiles para estructuras fluoradas complejas.

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