Patent ID: 6392111
Filing Date: 2002-05-21
Classification: C07B,C07C

Abstract:
A process for the preparation of olefin-substituted aromatics or heteroaromatics of formula III wherein Ar represents substituted or unsubstituted aryl or heteroaryl residues, and R1, R2 and R3 independently represent hydrogen, alkyl-(C1-C8), phenyl, 1- or 2-naphthyl, vinyl, O-alkyl-(C1-C8), O-phenyl, CN, CO2H, CO2-alkyl-(C1-C8), CO2-phenyl, CONH2, CONH-alkyl-(C1-C5), CON(alkyl)2-(C1-C5), fluoro, chloro, PO(phenyl)2, PO(alkyl)2-(C1-C5), CO-phenyl, CO-alkyl-(C1-C5), NH-alkyl-(C1-C4), SO3H, PO3H, SO3-alkyl-(C1-C4) or SO2-alkyl-(C1-C4), or R1+R2=(CH2)n, or R2+R3=(CH2)n wherein n=2-16, by reacting aromatics or heteroaromatics of formula I wherein Ar has the same meaning as in formula III and X represents chloro, bromo, OSO2CH3, OSO2-tolyl, OSO2CF3 or OSO2C4F9 or N2+Clâˆ’, with olefins of formula II wherein R1, R2 and R3 have the same meanings as in formula III, in the presence of palladium catalysts, characterized in that a palladium(II) compound of general formula PdXY or its CH3CN or C6H5CN complexes, wherein X=Y=Cl, Br, I, NO3, RCO2 (R=C1-C22, CF3, CCl3, CH2OCH3, C6H5) or RSO3 (R=C1-C22, CF3, C4F9, CCl3, C6H5, p-CH3C6H4), is used as the catalyst, and the reaction is performed in the absence of phosphonium salts and phosphanes and in the presence of a nitrogen-containing additive and a solvent and a base at temperatures of from 60Â° C. to 180Â° C.