Verfahren zur Herstellung von aromatischen Olefinen mittels Katalyse durch Palladaphosphacyclobutane

A process is disclosed for preparing monofunctional, bifunctional and polyfunctional aromatic olefins of formula (I), in which R to R independently represent hydrogen, C1-C8-alkyl, (C1-C8)-alkoxy, (C1-C8)-acyloxy, O-phenyl, phenyl, fluorine, chlorine, bromine, iodine, OH, NO2, OSO2CF3, CN, COOH, CHO, SO3H, SO2R, SOR, NH2, NH-(C1-C8)-alkyl, N-(C1-C8)-alkyl2-, CHal3, NHCO-(C1-C4)-alkyl, N-(C1-C4)-alkyl-CO-(C1-C4)-alkyl, COO-(C1-C8)-alkyl, CONH2, CO-(C1-C8)-alkyl, NHCOH, NCOO-(C1-C4)-alkyl, CO-phenyl, COO-phenyl, CHCH-CO2-(C1-C8)-alkyl, CHCHCO2H, PO-phenyl2, PO-(C1-C4)-alkyl2, OSO2-phenyl, OSO2CH3, or of formula (Ia), in which R stands for hydrogen, (C1-C8)-alkyl, phenyl, O-(C1-C8)-alkyl, fluorine; R and R independently represent hydrogen, CN, CO2H, CO2-(C1-C8)-alkyl, CONH2, CONH-(C1-C4)-alkyl, CON(C1-C4)-(alkyl)2, fluorine, CO2-phenyl, alkyl, (C1-C8)-phenyl, PO(phenyl), PO-(C1-C4)-(alkyl)2, CO-phenyl, CO-(C1-C4)-alkyl, O-(C1-C4)-alkyl, NH-(C1-C4)-alkyl, PO3H, SO3H, SO3-(C1-C4)-alkyl, SO2-(C1-C4)-alkyl, O-phenyl, (C1-C8)-alkyl, by reacting halogenated aromatic compounds of general formula (II) with olefins of general formula (III), in which R to R have the above-mentioned meanings, X having the same meaning as radicals R to R . This process is characterised in that a palladium compound of general formula (IV) is used as catalyst. In formula (IV), R , R independently represent hydrogen, (C1-C4)-alkyl, (C3-C12)-cycloalkyl, (C1-C4)-alkoxy, fluorine, N-(C1-C4)-(alkyl)2, CO2-(C1-C4)-alkyl, OCO-(C1-C4)-alkyl or aryl; R , R , R , R independently represent (C1-C8)-alkyl, (C3-C12)-cycloalkyl, aryl; or in which R and R , R or R and R or R , R and R , R or R and R or R , R and R form together an aliphatic ring, or in which R and R , R or R and R or R form together an aromatic ring, and Y stands for an anion of an inorganic or organic acid.