Process for preparing substituted benzyl compounds and toluene derivatives

A process for preparing compounds of the formula (IV) 6

• which comprises, in a process step 1, coupling an aromatic of the formula (II) bearing a group A and a leaving group LG located in the ortho, meta or para position relative thereto with an organoboron compound of the formula (I) in the presence of a palladium and/or nickel catalyst and a base to form a compound of the formula (III), 7
• where
• R is an unsubstituted or substituted aryl or heteroaryl radical, an unbranched or branched (C1-C18)-alkyl radical, an unsubstituted or substituted (C2-C8)-alkenyl radical or an unsubstituted or substituted (C2-C8)-alkynyl radical,
• Q1, Q2 are identical or different and are each OH, (C1-C4)-alkoxy, (C1-C4)-alkyl, phenyl or halogen, together form a (C1-C4)-alkylenedioxy group, which may be unsubstituted or substituted by from 1 to 4 (C1-C4)-alkyl groups, or a 1,2-phenylene dioxy group or together with the boron atom are part of a boroxin ring of the formula (V), where the radicals R are identical or different, 8
• A is a cyano group or a carbonyl function of the formula COR1, where R1 is H, an unbranched or branched (C1-C8)-alkyl radical or an unsubstituted or substituted aryl or heteroaryl radical,
• LG is a leaving group,
• X is hydrogen or a substituent selected from the group consisting of aryl, substituted or unsubstituted, (C1-C8)-alkyl, branched or unbranched, (C1-C8)-alkenyl, branched or unbranched, (C1-C8)-alkynyl, branched or unbranched, (C1-C8)-alkoxy, (C1-C8)-acyloxy, Ophenyl, fluorine, chlorine, NO2, NH2, NHalkyl-(C1-C8), Nalkyl2-(C1-C8), OH, CN, CHO, COOH, SO3H, SO3-alkyl-(C1-C8), SO2NH2, SO2N(alkyl-(C1-C8))2, SO2-alkyl-(C1-C8), COO-alkyl-(C1-C8), CONH2, CO-alkyl-(C1-C8), NHCHO, CF3, 5-membered heteroaryl or
• 6-membered heteroaryl, or in each case two of the substituents X together form an aliphatic or aromatic 5-6-membered carbocyclic ring or heterocyclic ring containing C, N, S and/or 0 atoms, where n can be 1, 2, 3 or 4,
• and, in a process step 2, reducing the compound of the formula (Ill) to give the compound of the formula (IV), where
• A′ is CH3, CH2NH2, CH2OH, CH(OH)R1 or CH2 R1,
• X′n is Xn or hydrogenated Xn and
• R′ is R or hydrogenated R.