Process for the preparation of mono-, bi- or poly-functional biaryls

A process for the preparation of a mono-, bi or poly-functional biaryl of the general formula I

• Ar—Ar′ (I)
• comprising reacting an aryl compound of formula II
• Ar—X (II)
• with an arylboronic acid of formula III
• Ar′—B(OR1)2 (III)
• in the presence of a catalyst,
• wherein the catalyst is a metal complex of the formula IV
• wherein in formulae I to IV
• Ar′ and Ar each independently of the other represents mono- or poly-cyclic aromatic that is optionally substituted and has up to 14 carbon atoms in the ring, or heteroaromatic that is optionally substituted and has from 5 to 10 atoms in the ring, of which up to four atoms independently of one another may be N, O or S,
• X represents I, Br, Cl, OSO2CF3, OSO2(aryl), OSO2(alkyl), N2+,
• M represents nickel, palladium or platinum,
• L represents a monodentate phosphoroorganic ligand PR6R7R8,
• A, B, C each independently of the others is a member selected from the group consisting of oxygen, sulfur, CH2, C(R9)a(R10)b group, N(R11)c, and Si (R12)d(R13)e wherein a, b, c, d, e may each independently of the others be 0 or 1, and when a, b, c, d, e of at least one of said members is 0, A, B and C can also be part of a ring system,
• x, y, z represent 0 or 1 and x+y+z=from 1 to 3,
• R1 represents hydrogen, alkyl, aryl or alkenyl, wherein in formula III B (OR1)2 can also form a ring system,
• R6 to R8 have the meanings of R1, or represent O-alkyl, O—C(O)-alkyl, or O-(aryl),
• R2 to R5 and R9R13 have the meanings of R1, or represent O-alkyl, O—C(O)-alkyl, O-(aryl), O—C(O)-aryl, F, Cl, OH, NO2, Si(alkyl)3, CF3, CN, CO2H, C(O)H, SO3H, NH2, NH(alkyl), N(alkyl)2, P(alkyl)2, SO2(alkyl), SO(alkyl), SO(aryl), SO2(aryl), SO3(alkyl), SO3(aryl), S-alkyl, S-aryl, S-alkenyl, NH—CO(alkyl), CO2(alkyl), CONH2, CO(alkyl), NHCOH, NHCO2(alkyl), CO(aryl), CO2(aryl), CH═CH—CO2(alkyl), CH═CO—CO2H, P(aryl)2, PO(aryl)2, PO(alkyl)2, PO3H and PO(O-alkyl)2,
• wherein alkyl represents hydrocarbon having from 1 to 10 carbon atoms and alkenyl represents mono- or poly-unsaturated hydrocarbon having from 1 to 10 carbon atoms, each of which may be branched and/or substituted by Cl, F, alkyl, O-alkyl, phenyl, O-phenyl, and aryl represents an optionally Cl-, F-, alkyl-, O-alkyl-, phenyl-, O-phenyl-substituted aromatic or heteroaromatic having from 5 to 10 atoms in the ring.