Then, various substituted 2-nitro fluorobenzenes 2 were examined (Figure ). The introduction of a third substituent did not affect the enantioselectivity, but the yield was affected by its electronic effects. For example, the 1,4difluoro-2-nitrobenzene gave product 3s in 91% yield with > 99% ee. When a third substituent with less electronegativity than the fluoro moiety was installed at the para-position of the benzene ring, the yields slightly decreased (Figure , 3t-3y vs. 3s). Besides the para-substituted 2-nitro fluorobenzenes, the meta-and ortho-substituted ones also gave the desired products in good yields with excellent enantioselectivities (Figure ). When two substituents were introduced simultaneously on the benzene ring, the combination of an electron-donating and electron-withdrawing group was necessary to obtain satisfactory yields (Figure ) because the increase of strong electron-withdrawing groups accelerated the generation of Narylation side products. Particularly, when 2,4-dinitro fluorobenzene was introduced as an arylation reagent, only the N-arylation byproduct was observed. For most substrates, the generation of N-functionalization side products was unavoidable. For example, accompanying the formation of C-functionalization products 3aa and 3ac, corresponding N-arylation side products were obtained in 25% and 30% yield, respectively.