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Un nuevo reactivo para difluorometilación directa

Yuta Fujiwara¹, Janice A Dixon, Rodrigo A Rodriguez

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Journal of the American Chemical Society

|January 11, 2012

Resumen

Un nuevo reactivo, el difluorometil zinc (DFMS), permite una difluorometilación eficiente de las moléculas orgánicas. Este proceso radical es suave, escalable y funciona para varios sustratos complejos como los heteroarenos y los tiolos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Química Medicinal Química medicinal es el campo de la Química Medicinal.
Ciencia de los materiales Ciencia de los materiales.

Sus antecedentes:

Los andamios moleculares que contienen alquilfluorino son cruciales en productos farmacéuticos y materiales.
El desarrollo de métodos eficientes para la introducción de grupos difluorometilo es un desafío continuo.

Objetivo del estudio:

Para reportar un nuevo reactivo, Zn(SO(2) CF(2) H) ((2) (DFMS), para la difluorometilación.
Para establecer un proceso de difluorometilación radical suave, escalable y quimioselectivo.

Principales métodos:

Difluorometilación radical utilizando el nuevo reactivo DFMS.
Aplicación a diversos sustratos orgánicos, incluidos los heteroarenos que contienen nitrógeno, los sistemas π conjugados y los tiolos.

Principales resultados:

DFMS facilita la difluorometilación innata bajo condiciones suaves y operacionalmente simples.
El método demuestra una amplia compatibilidad y escalabilidad de sustrato.
El análisis regioquímico indica que el radical CF(2) H exhibe un carácter nucleófilo.

Conclusiones:

DFMS es un reactivo versátil para la introducción del grupo difluorometilo.
Este método ofrece una herramienta valiosa para la síntesis de compuestos orgánicos fluorados.
La naturaleza nucleofílica del radical CF(2) H proporciona información sobre los mecanismos de reacción.

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