δ-Regioselective heteroarylation of free alcohols through 1,5-hydrogen-atom transfer

Abstract

An efficient silver-catalyzed δ-regioselective C(sp³)–H heteroarylation of free alcohols has been developed. Various alcohols reacted with quinolines, isoquinoline, pyridines, pyrimidine, phthalazine, 4-hydroxyquinazoline, acridine, quinoxaline and pyrazine to give the corresponding C(sp²)–H alkylation products in 31–89% yields. Notably, all types (1°, 2°, and 3°) of δ-C(sp³)–H bonds in the alcohols could be regioselectively activated. This protocol provides a platform to access divergent functionalizations of alcohols and heteroaryls by forming the challenging δ-selective C(sp³)–C(sp²) bond.