Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ-Fluorinated Ketones

A regioselective synthesis of beta- and gamma-fluorinated ketones via silver-catalyzed ring opening is described. A variety of beta- and gamma-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduction of a fluorine atom into complex molecules. Preliminary mechanistic studies suggest that a radical-mediated sequential C-C bond cleavage and C-F bond formation pathway is involved.