Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile

Abstract

The efficient regioselective C–H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O₂ and N₂ atmospheres, respectively. Using 2,2′-azobisisobutyronitrile (AIBN) as a radical precursor, the protocols afforded the corresponding products in moderate to good yields with broad substrate generality through Cu(OAc)₂ or NiSO₄ catalysis. Furthermore, the single electron transfer (SET) mechanism was proposed via a radical coupling pathway.