Deprotonation of N-(2-fluorophenyl)-2,6-diisopropylaniline (H[(PrAr)-Pr-i-NF]) with 1 equiv of n-BuLi in toluene at -35 degrees C produced cleanly [(PrAr)-Pr-i-NF]Li. Subsequent recrystallization of [(PrAr)-Pr-i-NF]Li in diethyl ether generated the bis(ether) adduct [(PrAr)-Pr-i-NF)Li(OEt2)(2). An X-ray study of [(PrAr)-Pr-i-NF]Li(OEt2)(2) showed it to be a four-coordinate species with the coordination of the fluorine atom to the lithium center. The reactions of [iPrAr-NF]Li with MCl4(THF)(2) (M = Zr, Hf), regardless of the stoichiometry employed, afforded the corresponding dichloride complexes [(PrAr)-Pr-i-NF](2)MCl2 (M = Zr, Hf). Alkylation of [(PrAr)-Pr-i-NF](2)MCl2 with a variety of Grignard reagents generated [(PrAr)-Pr-i-NF](2)MR2 (M = Zr, Hf; R = Me, i-Bu, CH2Ph). The X-ray structures of [(PrAr)-Pr-i-NF](2)ZrCl2, [(PrAr)-Pr-i-NF](2)HfCl2, [(PrAr)-Pr-i-NF](2)ZrMe2, [(PrAr)-Pr-i-NF](2)Zr(iBu)(2), and [(PrAr)-Pr-i-NF](2)Hf(CH2Ph)(2) are all indicative of the coordination of the fluorine atoms to these group 4 metals, leading to a C-2-symmetric, distorted octahedral geometry for these molecules.