Iodine-Catalyzed Aerobic Diazenylation–Amination of Indole Derivatives

A mild
strategy for consecutive diazenylation and amination of indole moieties has been
demonstrated. The functionalization occurs at C3 and C2 carbon atoms,
respectively, at the indole scaffold in the presence of catalytic
iodine and air at 40 °C in the 1,1,1,3,3,3-hexafluoroisopropanol
(HFIP) solvent. It is noteworthy that the aromatic amines are generated
in situ by the reaction of aryl hydrazine with iodine. In general,
bright red products are obtained in moderate to good yield. Control
reactions are conducted to establish the reaction mechanism.