Preparation of substituted aromatic compounds

A process for preparing compounds of the formula (II),

• where the substituents R1 to R5 are each independently H, CH3, straight-chain or branched C1–C8-alkyl, CH(OC1–C6-alkyl)2, CH(C1–C5-alkyl)(OC1–C5-alkyl), CH2(OC1–C5-alkyl), CH(CH3)(OC1–C5-alkyl), C1–C8-alkoxy, N(C1–C5-alkyl)2, phenyl, substituted phenyl, aryl, heteroaryl, S(C1–C5-alkyl) or a radical Caryl, alkyl, and the symbols X1 to 5 are each carbon with at least one X1-5 being nitrogen or with at least one X1-5 being nitrogen and X1R1 and X2R2 together are O, NH, N(C1–C5-alkyl), N(C═O—C1–C5-alkyl), N(SiR3)2 or S,
• or where neighboring radicals R1 to R5 form the following structural unit,
• where X6 to X9 and R6 to R9 have the same meaning as X1 to X5 and R1 to R5 and
• the radical Caryl, alkyl is straight-chain or branched, substituted or unsubstituted C1–C8-alkyl, 1-hydroxyalkyl having from 1 to 8 carbon atoms, CN, 2-hydroxyalkyl having from 2 to 5 carbon atoms, 3-hydroxyalkyl having from 3 to 5 carbon atoms, 1-NHR-, CH(OC1–C5-alkyl)2, C(C1–C5-alkyl)(OC1–C5-alkyl), CH2(OC1–C5-alkyl), CH(CH3)(OC1–C5-alkyl), C1–C5-alkoxy, N(C1–C5-alkyl)2, phenyl, substituted phenyl, aryl, heteroaryl, CO2H, CO2alkyl, (C═O)0.5, substituted 1-vinylalkyls, CH3—C(═O), R—C(═O) or CHO, wherein R is an alkyl having from 1 to 5 carbon atoms,
• which comprises reacting chloro- or fluoroaromatics of the formula (I) with carbon electrophiles and lithium metal.