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Diazometilación de enlaces de arilo C-H catalizados por fotorredóxido en etapa tardía con reactivos de carbono

Alessio Puggioli^1,2, Liyin Jiang¹, Ana G Herraiz¹

¹Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology, Països Catalans 16, 43007 Tarragona, Spain.

Journal of the American Chemical Society

|March 21, 2025

Resumen

Los investigadores desarrollaron nuevos compuestos diazo para la construcción de centros quirales en etapa tardía. Esta estrategia de reactivo de carbono atómico utiliza la catálisis fotorredóxica para la funcionalización eficiente de C-H en el descubrimiento de fármacos.

Área de la Ciencia:

Química orgánica
Catálisis
Química medicinal

Sus antecedentes:

La funcionalización en etapa tardía es crucial para el descubrimiento y desarrollo de fármacos.
Los métodos eficientes para la construcción de centros quirales son muy buscados.
Los nuevos reactivos de carbono atómico pueden permitir nuevas vías sintéticas.

Objetivo del estudio:

Introducir una nueva clase de compuestos diazo como reactivos atómicos de carbono.
Para demostrar su utilidad en la última etapa de la construcción de centros quirales.
Aplicar esta metodología a las moléculas de fármacos y a las materias primas aromáticas.

Principales métodos:

Utilizando la catálisis fotorredóxica para la diazometilación de C-H.
Empleando grupos de salida redox ortogonales en los compuestos diazo.
Aprovechando las funcionalizaciones de éster diazo y redox-activo establecidas.
Síntesis paralela automatizada para la generación de bibliotecas.

Principales resultados:

Construcción exitosa en etapa tardía de centros quirales con enlaces arilo C-H.
Generación de ésteres redox activos sustituidos por diazometil a través de la catálisis fotoredox.
Amplia aplicabilidad del nuevo reactivo con diversas funcionalidades.
Utilidad demostrada en la síntesis de una biblioteca de derivados de Fenofibrato.

Conclusiones:

Los nuevos compuestos diazo sirven como reactivos de carbono atómico efectivos para la construcción de centros quirales.
La catálisis fotorredóxica es clave para permitir una eficiente funcionalización de C-H.
La estrategia desarrollada es aplicable a las moléculas complejas y a los esfuerzos de descubrimiento de fármacos.

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