Abstract Reaction of N, N-dimethylaniline, N, N-dimethylnaphthalen-1-amine and 1, 8-bis (dimethylamino) naphthalene (proton sponge) with 1-chloromethyl-4-fluorodiazonia-bicyclo [2.2. 2] octane bis (tetrafluoroborate)(Selectfluor) and N-fluorobenzenesulfonimide (NFSI) has been studied under various conditions. Unlike the proton sponge, which is fluorinated rather selectively at the ortho-position to NMe 2 group, producing 2-fluoro derivatives in ...