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Reorganización de sonrisas de inamida desencadenada por el acoplamiento regioselectivo cetil-inamida mediado por luz

Ze-Shu Wang¹, Yang-Bo Chen¹, Hao-Wen Zhang¹

¹iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, and College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China.

Journal of the American Chemical Society

|February 1, 2020

Resumen

Este estudio introduce un nuevo radical Smiles catalizado por fotorreducción de los ynamidos, lo que permite una síntesis eficiente de 2-benzhidrilindoles y 3-benzhidrilisoquinolinas en condiciones suaves.

Área de la Ciencia:

Química orgánica
Metodología sintética
Catálisis por fotorreducción

Sus antecedentes:

El reordenamiento de sonrisas radicales es una herramienta sintética crucial.
Los métodos anteriores se limitaban a los radicales amidil intermedios.
Se necesitan nuevos productos intermedios radicales para aplicaciones más amplias.

Objetivo del estudio:

Para desarrollar una nueva reorganización radical de sonrisas usando ynamides.
Establecer un método catalizado por fotorreducción para la síntesis de valiosos derivados de indol e isoquinolina.
Explorar el alcance y el mecanismo de esta nueva transformación.

Principales métodos:

Catálisis fotorredóxica para el acoplamiento regioselectivo de cetil-inamida.
Sonrisas radicales reorganización de las confusiones.
Síntesis divergente de las isoquinolinas a través de la oxidación deshidrogenativa.

Principales resultados:

La primera reorganización radical de Smiles fue reportada.
Se logra una síntesis eficiente de 2-benzhidrilindoles con un amplio alcance de sustrato.
El acceso a las 3-benzhidrilisoquinolinas se demuestra a través de una secuencia de dos pasos.
La catálisis fotorredóxica intermolecular con fuentes radicales externas también fue exitosa.

Conclusiones:

El método desarrollado proporciona un fácil acceso a valiosos compuestos heterocíclicos.
La reacción se produce a través de radicales cetilo y radicales α-imino de carbono intermedios.
Este trabajo amplía el alcance de la reorganización de sonrisas radicales y la química ynamida.

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