Conversion of Aryl Azides to Aminopyridines
Sajan C. Patel, Noah Z. Burns
Abstract
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.
Topics & Concepts
AminopyridinesChemistryPyridineArylBenzeneCombinatorial chemistryRing (chemistry)AzideNitrogenPhotochemistryMedicinal chemistryOrganic chemistryAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions