Method for metal-organic production of organic intermediate products by means of aryl lithium-bases

A process for preparing compounds of the formulae (VII) and (VIII) via aryllithium compounds of the formulae (V) and (VI) and reaction of these with suitable electrophiles, aryl halides of the formula (I) are reacted with lithium metal to generate a lithium compound (II), this is used for deprotonating the aromatic substrate (III) or (IV), and is finally converted by addition of the electrophilic component into the target compound of the formula (VII) or (VIII) (equation 1), and the steps 1 to 3 are carried out as a one-pot reaction,

• Step 1:
• Generation of the Base
• Step 2:
• Deprotonation of the Substrate
• Step 3:
• Reaction of the Aryllithium Compound with an Electrophile
• (Equation 1)
• where Ar is phenyl, alkyl-substituted phenyl, fluorine- or chlorine-substituted phenyl, naphthyl-, alkyl-substituted naphthyl or is biphenyl, Hal is a halogen selected from the group consisting of fluorine, chlorine, bromine, iodine, and mixtures thereof,
• the radicals X1-4 are, independently of one another, either carbon, XiRi (i=1-4) can symbolize nitrogen, or two radicals XiRi which are adjacent or connected via a formal double bond can together be O (furans), S (thiophenes), NH or NRi (pyrroles),
• Z is, in the case of benzoidal aromatics, a group which activates the ortho position, for example CF3, OCF3, Cl, F, Oalkyl, Oaryl, Salkyl, Saryl, CH2OH, CH2OR, CH(OR)2, CONR2, NHR, NR2, or in the case of heterocycles has the same meaning as R1-4,
• the radicals R14 are substituents selected from the group consisting of hydrogen, methyl, primary, secondary or tertiary, cyclic or acyclic alkyl radicals having from 2 to 12 carbon atoms, substituted cyclic or acyclic alkyl groups, alkoxy, dialkylamino, alkylamino, arylamino, diarylamino, phenyl, substituted phenyl, alkylthio, diarylphosphino, dialkylphosphino, dialkylaminocarbonyl or diarylaminocarbonyl, monoalkylaminocarbonyl or monoarylaminocarbonyl, CO2alkyl, CO2−, 1-hydroxyalkyl, 1-alkoxyalkyl, fluorine or chlorine, CN or heteroaryl, where two adjacent radicals R1-4 can together correspond to a fused-on aromatic or aliphatic ring,
• and wherein the electrophile is any electrophilic component which can be reacted with aryllithium compounds.