Unlocking electrophilic N-aryl intermediates from aryl azides, nitroarenes, and aryl amines in cyclization-migration reactions

An Account of our development of reactions to construct N-heterocycles by triggering cyclization-migration tandem reactions from aryl azides, nitroarenes, and aryl amines is described. The reactivity patterns of metal N-aryl nitrenes, nitrosoarenes, N-aryl nitrogen radical anions, and N-aryl nitrenoids are compared. 1. Introduction 2. Unlocking the reactivity embedded in aryl azides 3. Exploiting the reactivity of nitrosoarenes generated from nitroarenes 4. Radical anion N-aryl nitrogen reactive intermediates from nitroarenes 5. Oxidation of aryl amines to access electrophilic N-aryl nitrenoids 6. Conclusion