Photochemistry

Azide

Alkyl

Nitrogen

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Chemistry

Aryl

Aminopyridines

Pyridine

Benzene

Ring (chemistry)

Journal of the American Chemical Society

A longstanding challenge in fundamental functional group interconversion has been the direct transformation of benzene into pyridine via nitrogen insertion and carbon deletion. Herein, we report a protocol for the transformation of aryl azides, easily accessible from their corresponding anilines, to 2-aminopyridines using blue light and oxygen. Mechanistic studies corroborate that the arene to pyridine conversion is achieved by nitrogen insertion into the benzene ring followed by oxidative carbon extrusion.

Conversion of Aryl Azides to Aminopyridines