Cycloaliphatic/aromatic diphosphines and use thereof in catalysis

A bidentate organophosphorus ligand of the formula (Ia) or (Ib),

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• where o and p can each be, independently of one another, 0 or 1, and
• Ar is part of a six-membered aromatic ring system or a 5-6-membered heteroaromatic ring system, where the heteroaromatic ring system can contain 1-3 nitrogen atoms, 1 oxygen atom or 1 sulfur atom in the positions A, B, D and E, and
• CyAli is part of a 5-6-membered cycloaliphatic or heterocycloaliphatic ring system, where the hetercycloaliphatic ring system can contain 1-2 heteroatoms from the group consisting of N, O, S in the positions F, G, H and I, and
• R1-R2 are each, independently of one another, C1-C24-alkyl, C3-C8-cycloalkyl, where the ring may also contain 1-2 heteroatoms selected from the group consisting of N, O and S;
• C6-C14-aryl, phenyl, naphthyl, fluorenyl, C2-C13-heteroaryl in which the number of heteroatoms selected from the group consisting of N, O, S can be 1-4, where the abovementioned groups may each be, independently of one another, monosubstituted or polysubstituted by hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C2-C9-heteroalkyl, C6-C8-aryl, phenyl, naphthyl, fluorenyl, C2-C6-heteroaryl, where the number of heteroatoms from the group consisting of N, O, S can be 1-4, C1-C10-alkoxy, C1-C9-trihalomethylalkyl, halo, hydroxy, trifluoromethylsulfonato, oxo, thio, thiolato, amino, C1-C8-substituted amino of the formulae NH2, NH-alkyl-C1-C8, NH-aryl-C5-C6, N-alkyl2-C1-C8, N-aryl2-C5-C6, N-alkyl3-C1-C8+, N-aryl3-C5-C6+, NH—CO-alkyl-C1-C8, NH—CO-aryl-C5-C6, cyano, carboxylato of the formulae COOH and COOQ, where Q is either a monovalent cation or C1-C8-alkyl;
• C1-C6-acyloxy, sulfinato, sulfonato of the formulae SO3H and SO3Q, where Q is either a monovalent cation, C1-C8-alkyl or C6-aryl;
• phosphato of the formulae PO3H2, PO3HQ and PO3Q2, where Q is either a monovalent cation, C1-C8-alkyl or C6-aryl;
• tri-C1-C6-alkylsilyl, where R1 or R2 together with the adjacent phosphorus atom may be joined to form a 4-8-membered aliphatic ring which may be substituted by linear or branched C1-C10-alkyl, C6-aryl, benzyl, C1-C10-alkoxy, hydroxy or benzyloxy, and
• R3-R14 are each, independently of one another, a hydrogen atom or C1-C24-alkyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, where the ring may also contain 1-2 heteroatoms from the group consisting of N, O and S;
• C6-C14-aryl, phenyl, naphthyl, fluorenyl, C2-C13-heteroaryl, where the number of heteroatoms selected from the group consisting of N, O, S can be 1-4, where the abovementioned groups may each be, independently of one another, monosubstituted or polysubstituted by hydrogen, C1-C20-alkyl, C2-C20-alkenyl, C1-C10-haloalkyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C2-C9-heteroalkyl, C1-C9-heteroalkenyl, C6-C8-aryl, phenyl, naphthyl, fluorenyl, C2-C6-heteroaryl, where the number of heteroatoms, in particular from the group consisting of N, O, S, can be 1-4, C1-C10-alkoxy, C1-C9-trihalomethylalkyl, trifluoromethyl, trichloromethyl, fluoro, chloro, bromo, iodo, hydroxy, trifluoromethylsulfonato, oxo, thio, thiolato, amino, C1-C8-substituted amino of the formulae NH2, NH-alkyl-C1-C8, NH-aryl-C5-C6, N-alkyl2-C1-C8, N-aryl2-C5-C6, N-alkyl3-C1-C8+, N-aryl3-C5-C6+, NH—CO-alkyl-C1-C8, NH—CO-aryl-C5-C6, cyano, carboxylato of the formulae COOH and COOQ, where Q is either a monovalent cation or C1-C8-alkyl;
• C1-C6-acyloxy, sulfinato, sulfonato of the formulae SO3H and SO3Q, where Q is either a monovalent cation, C1-C8-alkyl or C6-aryl;
• phosphato of the formulae PO3H2, PO3HQ and PO3Q2, where Q is either a monovalent cation, C1-C8-alkyl or C6-aryl;
• or tri-C1-C6-alkylsilyl, and two of these substituents may also be bridged, and
• m, n are each, independently of one another, 1 or 0, and
• P is a trivalent phosphorus atom.