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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… Click to show full 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.
Journal Title: Organic chemistry frontiers
Year Published: 2020
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