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

The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O(2)and N(2)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 NiSO(4)catalysis. Furthermore, the single electron transfer (SET) mechanism was proposedviaa radical coupling pathway.