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

An efficient silver-catalyzed d-regioselective C(sp(3))-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(sp(2))-H alkylation products in 31-89% yields. Notably, all types (1 degrees, 2 degrees, and 3 degrees) of d-C(sp(3))-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 d-selective C(sp(3))-C(sp(2)) bond.

Automated summary

An efficient silver-catalyzed d-regioselective C(sp(3))-H heteroarylation of free alcohols has been developed, allowing for selective activation of different types of d-C(sp(3))-H bonds in alcohols and providing a new platform for diverse functionalizations of alcohols and heteroaryls.