Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile
Chunxia Wen, Rong‐Lin Zhong, Zengxin Qin, Mengfei Zhao, Jizhen Li
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.
Topics & Concepts
AzobisisobutyronitrileRegioselectivityChemistryCatalysisCombinatorial chemistryOrganic chemistryPolymerizationPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques