AgII-Mediated Synthesis of β-Fluoroketones by Oxidative Cyclopropanol Opening

A regioselective synthesis of beta-fluorinated ketones by silver(II)-mediated ring opening is described. Commercially available AgF2 serves as both an oxidant and fluorine-atom source. A variety of beta-fluorinated ketones are efficiently prepared from tertiary cyclopropanol precursors, offering a straightforward approach for the introduction of a fluorine atom at a remote site. Selectivity is observed in the site of bond cleavage, which leads to fluorination at the more substituted site. A radical mediated sequential homolytic C-C bond cleavage and C-F bond formation is suggested.