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Acoplamientos cruzados C-N para la diversificación en fase tardía selectiva por medio de sales de sulfonio de arilo

Pascal S Engl¹, Andreas P Häring¹, Florian Berger¹

¹Max-Planck-Institut für Kohlenforschung , Kaiser-Wilhelm Platz 1 , D-45470 Mülheim an der Ruhr , Germany.

Journal of the American Chemical Society

|August 15, 2019

Resumen

Este estudio introduce nuevas reacciones de acoplamiento cruzado C-N utilizando sales de tiantenio de arilo, lo que permite una funcionalización eficiente de aminas y heterociclos. Este método es valioso para la modificación tardía de moléculas complejas en el descubrimiento de fármacos.

Área de la Ciencia:

Química orgánica
Química sintética
Química medicinal

Sus antecedentes:

La funcionalización directa C-H ofrece una ruta eficiente a las moléculas complejas.
Las reacciones de acoplamiento son fundamentales en la síntesis orgánica.
Las sales de tiantenio de arilo son reactivos emergentes en la química orgánica.

Objetivo del estudio:

Desarrollar nuevas reacciones de acoplamiento cruzado C-N utilizando sales de tiantenio de arilo.
Explorar la formación selectiva del sitio de estas sales a través de la funcionalización directa C-H.
Demostrar la utilidad de esta metodología para la funcionalización en etapa tardía de moléculas similares a fármacos.

Principales métodos:

Funcionalización de C-H selectiva del sitio para generar sales de tiantenio de arilo.
Reacciones de acoplamiento cruzado C-N con un rango diverso de nucleófilos de nitrógeno.
Aplicación del método desarrollado a moléculas pequeñas complejas.

Principales resultados:

Síntesis exitosa de diversas sales de tiantenio de arilo a través de la funcionalización directa de C-H.
Se ha demostrado un amplio espectro de N-nucleófilos, incluidas las aminas primarias/secundarias y los N-heterociclos.
Validación del método para la funcionalización en etapa tardía de compuestos complejos similares a fármacos.

Conclusiones:

Se ha establecido un método novedoso y versátil para el acoplamiento cruzado C-N.
La funcionalización directa C-H proporciona un acceso eficiente a los principales intermediarios de tiantenio.
La metodología tiene un potencial significativo para la química medicinal y los esfuerzos de descubrimiento de medicamentos.

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