| US 7,589,081 B2 | ||
| Nitrogen-containing monodentate phosphines and their use in catalysis | ||
| Alexander Zapf, Rostock (Germany); Mark Sundermeier, Zürich (Switzerland); Ralf Jackstell, Cuxhaven (Germany); Matthias Beller, OB Nienhagen (Germany); Thomas Riermeier, Flörsheim (Germany); Axel Monsees, Frankfurt (Germany); and Uwe Dingerdissen, Seeheim (Germany) | ||
| Assigned to DEGUSSA GmbH, Duesseldorf (Germany) | ||
| Appl. No. 10/554,603 PCT Filed May 03, 2004, PCT No. PCT/EP2004/004644 § 371(c)(1), (2), (4) Date Oct. 27, 2005, PCT Pub. No. WO2004/101581, PCT Pub. Date Nov. 25, 2004. |
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| Claims priority of application No. 103 22 408 (DE), filed on May 16, 2003. | ||
| Prior Publication US 2007/0123707 A1, May 31, 2007 | ||
| Int. Cl. A61K 31/675 (2006.01); C07F 9/28 (2006.01) | ||
| U.S. Cl. 514—89 [514/91; 546/22; 548/111; 548/412] | 18 Claims |
1. A phosphane ligand of formula (I)
![]() wherein
X independently of Y represents a nitrogen atom or a C-R2 group and
Y independently of X represents a nitrogen atom or a C-R9 group,
R1 for each of the two R1 groups independently of the other represents a radical selected from the group consisting of
a C1-C24-alkyl radical,
a C3-C20-cycloalkyl radical,
which comprises monocyclic, bicyclic, and tricyclic cycloalkyl radicals,
a C5-C14-aryl radical,
which comprises a phenyl radical, a naplithyl radical, and a fluorenyl radical, with the proviso that if one R1 is a non-substituted phenyl, the second R1 cannot be a non-substituted phenyl,
and a C2-C13-heteroaryl radical,
wherein the heteroatoms comprise nitrogen, oxygen, sulfur, or a combination thereof and wherein the number of heteroatoms
is from 1 to 2,
wherein the two radicals R1 may be linked to one another,
wherein the above-mentioned radicals R1 may each be mono- or poly-substituted independently of one another by substituents selected from the group consisting of hydrogen,
a C1-C20-alkyl radical, a C2-C20-alkenyl radical, a C3-C8-cycloalkyl radical, a C2-C9-hetero-alkyl radical, a C5-C10-aryl radical, a C2-C9-heteroaryl radical,
wherein the heteroatoms comprise nitrogen, oxygen, sulfur, or a combination thereof
and wherein the number of hetero atoms is from 1 to 4,
a C1-C20-alkoxy radical, a C1-C10-haloalkyl radical, a hydroxyl radical, a NH—(C1-C20-alkyl) radical, a NH—(C5-C10-aryl) radical, a N (C1-C20-alkyl)2 radical, a N (C1-C20-alkyl) (C5-C10-aryl) radical, a N(C5-C10-aryl)2 radical, a N(C1-C20-alkyl/C5-C10-aryl3)3+ radical, a NH—CO—C1-C20-alkyl radical, a NH—CO—C5-C10-aryl radical, a COOH radical, a COOQ′ radical, a C1-C6-acyloxy radical, a sulfinato radical, a —SO3H radical, a SO3Q″ radical and a tri-C1-C6-alkylsilyl radical,
wherein Q′ represents either a monovalent cation or a C1-C8-alkyl radical and Q″ represents either a monovalent cation, a C1-C20-alkyl radical, or a C5-C10-aryl radical,
wherein two of the mentioned substituents may be bridged with one another,
R2-R9 independently represent hydrogen, an alkyl radical, an alkenyl radical, a cycloalkyl radical, an aromatic or heteroaromatic
aryl radical, an O-alkyl radical, an NH-alkyl radical, an N-(alkyl)2 radical, an O-(aryl) radical, an NH-(aryl) radical, an N-(alkyl)(aryl) radical, an O—CO-alkyl radical, a O—CO-aryl radical,
a F, a Si(alkyl)3 radical, a CF3 radical, a CN radical, a CO2H radical, a COH radical, an SO3H radical, a CONH2 radical, an CONH(alkyl) radical, a CON(alkyl)2 radical, an SO2(alkyl) radical, a SO(alkyl) radical, a SO(aryl) radical, a SO2(aryl) radical, a SO3(alkyl) radical, a SO3(aryl) radical, an S-alkyl radical, an S-aryl radical, a NH—CO(alkyl) radical, a C2(alkyl) radical, a CONH2 radical, a CO(alkyl) radical, a NHCOH radical, a NHCO2(alkyl) radical, a CO(aryl) radical, or a C2(aryl) radical,
wherein two or more adjacent radicals, each independently of the other(s), may also be linked to one another so that a condensed
ring system is present and
wherein in R2 to R9
an alkyl radical comprises a hydrocarbon radical comprising from 1 to 20 carbon atoms which may be linear or branched, an
alkenyl radical represents a mono- or poly-unsaturated hydrocarbon radical comprising from 2 to 20 carbon atoms which may
in be linear or branched, a cycloalkyl radical comprises a hydrocarbon comprising from 3 to 20 carbon atoms, an aryl radical
comprises a 5- to 14-membered aromatic radical, wherein from one to four carbon atoms in the aryl radical may be replaced
by hetero atoms wherein the heteroatoms are nitrogen, sulfur, and oxygen so that a 5- to 14-membered heteroaromatic radical
is present, wherein the radicals R2 to R9 may also carry further substituents as defined for R1.
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