Selective introduction of fluorine atoms to the tert-carbons of functionalized adamantanes by BrF3

The direct fluorination reaction of the functionalized adamantanes was achieved by using BrF3. In the reaction with methyl adamantane-1-caroxylate 1 and dimethyl adamantane-1,3-dicarboxylate 3, three and two fluorine atoms, respectively, were introduced selectively to their tert-carbons. On the other hand, in the reactions with 1-acetoxymethyladamantane 5, and 2-adamantanone 9, not only the expected fluorination of their tert-carbons, but also unexpected reactions such as fluorination of carbonyl functionality occurred.