Patent US5371256A successfully refreshed from Google Patents.
US5371256A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Ferrocenyl diphosphines as ligands for homogeneous catalysts
Assignee: Novartis Corp
•
Filing: 1993-03-26
•
Granted: 1994-12-06
•
Expires: 2013-03-26
Abstract
Abstract Compounds of formula I ##STR1## wherein R 1 is C 1 -C 8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups; R 2 and R 3 are identical and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl or C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C 12 cycloalkyl, or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M,--NR 7 R 8 and --[.sup.⊕ NR 7 R 8 R 9 ]X.sup.⊖ ; or R 2 and R 3 are different and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C 12 cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M 2 , --NR 7 R 8 and --[.sup.⊕NR 7 R 8 R 9 ]X.sup.⊖ ; or the group --PR 2 R 3 is a radical of formula II ##STR2## and R 4 , R 5 and R 6 are each independently of one another C 1 -C 12 alkyl or phenyl, R 7 and R 8 are H, C 1 -C 2 alkyl, phenyl or R 7 and R 8 , taken together, are tetramethylene, pentamethylene or 3-oxa-1,5-pentylene, R 9 is H or C 1 -C 4 alkyl, M is H or an alkali metal, X.sup.⊖ is the anion of a monobasic acid, and * is a stereogenic carbon atom, in the form of their racemates and diastereoisomers or mixtures of diastereoisomers. Rhodium and iridium complexes with these ligands are suitable for use as homogeneous enantioselective catalysts for the hydrogenation of prochiral compounds containing carbon double bonds or carbon/hetero atom double bonds.
Inventors
- 👤 Antonio Togni
- 👤 Felix Spindler
- 👤 Nadia Zanetti
- 👤 Amina Tijani
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 02:29
CPC Classifications
C; C07; C07F; C07F17/00; C07F17/02; B; B01; B01J; B01J31/00; B01J31/16; B01J31/22; B01J31/2282; B01J31/2291; B01J31/2295; B01J31/24; B01J31/2404; B01J31/2409; B01J31/2442; B01J31/2461; B01J31/2471; C07C; C07C209/00; C07C209/44; C07C209/52; C07C231/00; C07C231/16; C07C231/18; C07C67/00; C07C67/30; C07C67/303; C07C67/31; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/643; B01J2231/645; B01J2531/00; B01J2531/02; B01J2531/0202; B01J2531/0205; B01J2531/0286; B01J2531/80; B01J2531/82; B01J2531/822; B01J2531/827; B01J2531/84; B01J2531/842; Y; Y10; Y10S; Y10S526/00; Y10S526/943
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
339 words
A compound of formula I ##STR6## wherein R 1 is C 1 -C 8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups; R 2 and R 3 are identical and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl or C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C 12 cycloalkyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M, --NR 7 R 8 and --[.sup.⊕ NR 7 R 8 R 9 ]X.sup.⊖ ; or R 2 and R 3 are different and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C.sub. 12 cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M 2 , --NR 7 R 8 and --[.sup.⊕ NR 7 R 8 R 9 ]X.sup.⊖ ; or the group --PR 2 R 3 is a radical of formula II ##STR7## and R 4 , R 5 and R 6 are each independently of one another C 1 -C 12 alkyl or phenyl, R 7 and R 8 are H, C 1 -C 12 alkyl, phenyl or R 7 and R 8 , taken together, are tetramethylene, pentamethylene or 3-oxa-1,5-pentylene, R 9 is H or C 1 -C 4 alkyl, M is H or an alkali metal, X.sup.⊖ is the anion of a monobasic acid, and * is a stereogenic carbon atom, in the form of the racemate or diastereoisomer or mixture of diastereoisomers.
Claim 2
Dependent Claim
339 words
A compound of formula I ##STR6## wherein R 1 is C 1 -C 8 alkyl, phenyl or phenyl which is substituted by 1 to 3 C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups; R 2 and R 3 are identical and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl or C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C 12 cycloalkyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M, --NR 7 R 8 and --[.sup.⊕ NR 7 R 8 R 9 ]X.sup.⊖ ; or R 2 and R 3 are different and are C 1 -C 12 alkyl, C 5 -C 12 cycloalkyl, C 1 -C 4 alkyl- or C 1 -C 4 alkoxy-substituted C 5 -C.sub. 12 cycloalkyl, phenyl or phenyl which is substituted by one to three identical or different members selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, --SiR 4 R 5 R 6 , halogen, --SO 3 M, --CO 2 M, --PO 3 M 2 , --NR 7 R 8 and --[.sup.⊕ NR 7 R 8 R 9 ]X.sup.⊖ ; or the group --PR 2 R 3 is a radical of formula II ##STR7## and R 4 , R 5 and R 6 are each independently of one another C 1 -C 12 alkyl or phenyl, R 7 and R 8 are H, C 1 -C 12 alkyl, phenyl or R 7 and R 8 , taken together, are tetramethylene, pentamethylene or 3-oxa-1,5-pentylene, R 9 is H or C 1 -C 4 alkyl, M is H or an alkali metal, X.sup.⊖ is the anion of a monobasic acid, and * is a stereogenic carbon atom, in the form of the racemate or diastereoisomer or mixture of diastereoisomers.
Claim 3
Dependent Claim
18 words
A compound of formula I according to claim 1, wherein R 1 is C 1 -C 4 alkyl.
Claim 4
Dependent Claim
16 words
A compound of formula I according to claim 2, wherein R 1 is methyl or ethyl.
Claim 5
Dependent Claim
35 words
A compound of formula I according to claim 1, wherein R 1 is phenyl or phenyl which is substituted by 1 or 2 C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups.
Claim 6
Dependent Claim
21 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are C 1 -C 8 alkyl.
Claim 7
Dependent Claim
22 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are identical and are isopropyl or tert-butyl.
Claim 8
Dependent Claim
24 words
A compound of formula I according to claim 1, wherein R 2 and R 3 as cycloalkyl contain 5 to 8 ring carbon atoms.
Claim 9
Dependent Claim
21 words
A compound of formula I according to claim 7, wherein R 2 and R 3 as cycloalkyl are cyclopentyl or cyclohexyl.
Claim 10
Dependent Claim
86 words
A compound of formula I according to claim 1, wherein R 2 and R 3 as substituted phenyl are selected from the group consisting of 2-methylphen-1-yl, 3-methylphen-1-yl, 4-methylphen-1-yl, 2- or 4-ethylphen-1-yl, 2- or 4-isopropylphen-1-yl, 2- or 4-tert-butylphen-1-yl, 2-methoxyphen-1-yl, 3-methoxyphen-1-yl, 4-methoxyphen-1-yl, 2- or 4-ethoxyphen-1-yl, 4-trimethylsilylphen-1-yl, 2- or 4-fluorophen-1-yl, 2,4-difluorophen-1-yl, 2-or 4-chlorophen-1-yl, 2,4-dichlorophen-1-yl, 2,4-dimethylphen-1 -yl, 3,5-dimethylphen-1-yl, 2-methoxy-4-methylphen-1-yl, 3,5-dimethyl-4-methoxyphen-1-yl, 3,5-dimethyl-4-(dimethylamino)phen-1-yl, 2- or 4-aminophen-1-yl, 2- or 4-methylaminophen-1-yl, 2- or 4-(dimethylamnio)phen-1-yl, 2- or 4-SO 3 H-phen-1-yl, 2- or 4-SO 3 Na-phen-1-yl, 2- or 4-[.sup.⊕ NH 3 Cl.sup.⊖ ]phen-1-yl, 3,4,5-trimethylphen-1-yl and 2,4,6-trimethylphen-1-yl.
Claim 11
Dependent Claim
37 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are identical substituents selected from the group consisting of cyclohexyl, 2- or 4-methylphen-1-yl, 2- or 4-methoxyphen-1-yl, 2- or 4-(dimethylamino)phen-1-yl, 3,5-dimethyl-4-(dimethylamino)phen-1-yl and 3,5-dimethyl-4-methoxyphen-1-yl.
Claim 12
Dependent Claim
44 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are different and R 2 is phenyl and R 3 is selected from the group consisting of cyclohexyl, 2- or 4-methylphen-1-yl, 2- or 4-methoxyphen-1-yl, 4-(dimethylamino)phen-1-yl, 3,5-dimethyl-4-(dimethylamino)phen-1-yl, 3,5-dimethyl-4-methoxyphen-1-yl and 4-tert-butyl-phen-1-yl.
Claim 13
Dependent Claim
21 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are identical substituents and are cyclohexyl.
Claim 14
Dependent Claim
23 words
A compound of formula I according to claim 1, wherein R 2 and R 3 are identical substituents and are tert-butyl or o-anisyl.
Claim 15
Dependent Claim
19 words
A compound of formula I according to claim 1, wherein R 2 is phenyl and R 3 is o-anisyl.
Claim 16
Dependent Claim
23 words
A compound of formula I according to claim 1, wherein R 1 is methyl and R 2 and R 3 are each cyclohexyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-12-05 | 1998-06-06 | 1998-12-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-12-05 | 2002-06-06 | 2002-12-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-12-05 | 2006-06-06 | 2006-12-06 | $7700.00 | Window Closed / Lapsed |