Patent DE-10052391-A1 (DE)
Title: New bidentate organophosphorus ligands with a chiral carbon center, used in complex compounds for use as catalysts in asymmetric reactions or polymerizations, especially asymmetric hydroformylation or hydrogenation
Inventor: BOSCH BORIS E
IPC: C07F15/06
Filed: 2000-10-20
Abstract: Bidentate organophosphorus ligands in which a diorganophosphino-alkyl group with a chiral carbon center is separated from another diorganophosphine group by 1-6 carbon atoms forming part of a non-aromatic, optionally cyclic, optionally heteroatom-containing system, a metallocene or an aromatic or heteroaromatic ring system, is new. Bidentate organophosphorus ligands of formula (I), in which a diorganophosphino-alkyl group with a chiral carbon center is separated from another diorganophosphine group by 1-6 carbon atoms forming part of a non-aromatic, optionally cyclic, optionally heteroatom-containing system, a metallocene or an aromatic or heteroaromatic ring system, is new. (R<1>Y)(R<2>Y)PXZ-C asterisk HR<3>-PR<4>R<5>  (I) R<1>-R<5> = H or a 1-50C carbon-containing group selected from 1-24C alkyl, 3-8C cycloalkyl or cycloalkenyl, 6-14C aryl, phenyl, naphthyl, fluorenyl and 2-13C heteroaryl with 1-4 N, O or S atoms (all optionally mono- or poly-substituted with 1-20C alkyl, 2-20C alkenyl, 1-10C haloalkyl, 3-8C cycloalk(en)yl, 2-9C heteroalkyl, 1-9C heteroalkenyl, 6-14C aryl, phenyl, naphthyl, fluorenyl, 1-7C heteroaryl (as above), 1-10C alkoxy, 1-9C trihalomethyl-alkyl, trifluoromethyl, trichloromethyl, fluoro, chloro, bromo, iodo, nitro, hydroxy, trifluoromethanesulfonyl, oxo, thio, thiolato, amino, mono-, di- or tri-(1-8C alkyl)-amino or -(2-8C alkenyl)-amino or -(6-8C aryl)-amino or -(1-8C alkyl)-(6-8C aryl)-amino, -CO-(6-8C aryl), cyano, carboxyl, COOR<8>, 1-8C acyloxy, sulfinato, sulfonato (SO3R<8>), PO3H2, PO3HR<8>, PO3(R<8>)2 or tri-(1-6C alkyl)-silyl, or optionally with two of these substituents as a bridge), or R<1> and R<2> or R<4> and R<5> may be combined to form a 4- to 8-membered ring; R<8> = a monovalent cation or 1-8C alkyl; X, Y = a direct P-C bond, -O-, -S- or -NR<6>- (or NR<7> for Y); R<6>, R<7> = as for R<1>-R<5>; Z = 1-6 carbon atoms linked by single or multiple bonds, linking the unit (R<1>Y)(R<2>Y)PX with the chiral carbon center C asterisk , where Z is part of an aliphatic, heteroaliphatic, cycloaliphatic, heterocycloaliphatic, olefinic, hetero-olefinic, cyclo-olefinic or heterocyclo-olefinic system, a metallocene or an aromatic or heteroaromatic ring system (with 1-4 N, O or S atoms), all optionally mono- or poly-substituted with groups as for R<1>-R<5> or directly with 1-10C alkoxy, 1-9C trihalomethyl-alkyl, CF3, CCl3, F, Cl, Br, I, NO2, OH, trifluoromethylsulfonato, oxo, thio, thiolato, NH2, NH(1-8C alkyl), NH(5-6C aryl), corresponding di-alkyl or di-aryl amino and quaternary groups, CN, COOH, COOR<8>, 1-6C acyloxy, sulfinato, SO3H, SO3R<8> (with R<8> = monovalent cation, 1-8C alkyl or 6C aryl), PO3H2, PO3HR<8>, PO3(R<8>)2, tri-(1-6C alkyl)-silyl, CONH2, NHCO(1-4C alkyl), CON(1-8C alkyl)2, CO(1-8C alkyl), COO(1-8C alk(en)yl), NHCOO(1-4C alkyl), CO(6-10C aryl), COO(6-10C aryl), -CH=CH-COO(18C alkyl) or -CH=CH-COOH; and P = trivalent phosphorus. An Independent claim is also included for complex compounds of formula (II) (MxPmLnSq)Ar  (II) M = a metal center; P = one or more bidentate ligands (I); L = organic and/or inorganic ligands; S = coordinating solvent molecules; A = non-coordinating anionic equivalents; x, m = less than or equal to 1; and n, q, r = 0 or more.