Electrophilic fluorination of N,N-dimethylaniline, N,N-dimethylnaphthalen-1-amine and 1,8-bis(dimethylamino)naphthalene with N-F reagents

An implication of modern N-F reagents (Selectfluor, NFSI and NFSI-ZrCl4) to benzene and naphthalene compounds with dimethylamino groups is described. The proton sponge demonstrates the highest ortho/para selectivity among studied dimethylaminoarenes, while the NFSI-ZrCl4 system provokes competitive chlorination of the aromatic ring.