Process for preparing aromatic olefins using palladacycle...

Details Process for preparing aromatic olefins using palladacycle... Process for preparing aromatic olefins using palladacycle...

C - Chemistry, Metallurgy

07

C

C07C 69/73 (2006.01) B01J 31/24 (2006.01) C07B 37/04 (2006.01) C07C 45/68 (2006.01) C07C 45/69 (2006.01) C07C 47/548 (2006.01) C07C 49/796 (2006.01) C07C 67/343 (2006.01) C07C 67/347 (2006.01) C07C 69/618 (2006.01) C07C 69/65 (2006.01) C07F 9/53 (2006.01)

Patent

CA 2152289

The invention relates to a process for preparing monofunctional, bifunctional or polyfunctional aromatic olefins of the formula (I) (see formula I) where R1a to R5a are, independently of one another, hydrogen, C1-C8-alkyl, alkoxy-(C1-C8), acyloxy-(C1-C8), O-phenyl, phenyl, fluorine, chlorine, bromine, iodine, OH, NO2, OSO2CF3, CN, COOH, CHO, SO3H, SO2R, SOR, NH2, NH-alkyl-(C1-C8), N-alkyl2-(C1-C8), CHal3, NHCO-alkyl-(C1-C4), N-alkyl-(C1-C4)-CO-alkyl-(C1-C4), COO-alkyl-(C1-C8), CONH2, CO-alkyl-(C1-C8), NHCOH, NCOO-alkyl-(C1-C4), CO-phenyl, COO-phenyl, CHCH-CO2-alkyl-(C1-C8), CHCHCO2H, PO-phenyl2, PO-alkyl2-(C1-C4), where one of the radicals R1a to R5a can also be (see formula V) R6a is hydrogen, alkyl (C1-C8), phenyl, O-alkyl-(C1-C8), fluorine, R7a and R8a are, independently of one another, hydrogen, CN, CO2H, CO2-alkyl-(C1-C8), CONH2, CONH-alkyl-(C1-C4), CON(alkyl)2-(C1-C4)-fluorine, CO2-phenyl, alkyl, (C1-C8)- phenyl, PO(phenyl), PO(alkyl-(C1-C4))2, CO-phenyl, CO-alkyl-(C1-C4), O-alkyl-(C1-C4), NH-alkyl-(C1-C4), PO3H, SO3H, SO3-alkyl (C1-C4), SO2-alkyl-(C1-C4), O-phenyl, by reaction of haloaromatics of the formula (II) (see formula II) with olefins of the formula (III) (see formula III) where R1a to R8a are as defined above, where one of the radicals R1a to R5a can also be X and X is iodine, bromine, chlorine, OSO2CF3, OSO2-phenyl, OSO2CH3, wherein a palladium compound of the formula (IV) (see formula IV) where R1, R2, R3, R4, R5, R6 are, independently of one another, hydrogen, (C1-C4)-alkyl, (C5-C8)-cycloalkyl, (C1-C4)- alkoxy, fluorine, NH2, NH-alkyl(C1-C4), N(alkyl)2-(C1-C4), CO2alkyl-(C1-C4), OCO-alkyl-(C1-C4) or phenyl, or R1 and R2, R2 and R3, R3 and R4, R5 and R6 together form an aliphatic or aromatic ring, and R7, R8 are (C1-C8)-alkyl, (C3-C12)-cycloalkyl, substituted or unsubstituted aryl and Y is an anion of an inorganic or organic acid, is used as catalyst.

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