CA1148564A - Asymmetric hydrogenation of prochiral olefines by complexes of transition metals immobilized in clay-like minerals - Google Patents

Asymmetric hydrogenation of prochiral olefines by complexes of transition metals immobilized in clay-like minerals

Info

Publication number: CA1148564A
Authority: CA; Canada
Prior art keywords: alpha; catalyst; clay; prochiral; acid
Prior art date: 1977-10-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000311978A

Other languages

English (en)

French (fr)

Inventor

Marcello Mazzei

Mario Riocci

Walter Marconi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Anic SpA

Original Assignee

Anic SpA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-10-17

Filing date

1978-09-25

Publication date

1983-06-21

1978-09-25 Application filed by Anic SpA filed Critical Anic SpA

1983-06-21 Application granted granted Critical

1983-06-21 Publication of CA1148564A publication Critical patent/CA1148564A/en

Status Expired legal-status Critical Current

Links

238000009876 asymmetric hydrogenation reaction Methods 0.000 title claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 title abstract description 5
239000011707 mineral Substances 0.000 title abstract description 5
229910052723 transition metal Inorganic materials 0.000 title description 4
150000003624 transition metals Chemical class 0.000 title description 4
239000003054 catalyst Substances 0.000 claims abstract description 23
239000010948 rhodium Substances 0.000 claims abstract description 11
229910052703 rhodium Inorganic materials 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
239000000758 substrate Substances 0.000 claims description 10
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 8
125000002091 cationic group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000005995 Aluminium silicate Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000001336 alkenes Chemical class 0.000 claims description 4
235000012211 aluminium silicate Nutrition 0.000 claims description 4
230000003100 immobilizing effect Effects 0.000 claims description 4
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
239000004927 clay Substances 0.000 claims description 3
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
230000006872 improvement Effects 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
150000003017 phosphorus Chemical class 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 abstract description 11
229910000271 hectorite Inorganic materials 0.000 abstract description 6
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 abstract description 5
239000000440 bentonite Substances 0.000 abstract description 2
229910000278 bentonite Inorganic materials 0.000 abstract description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 5
230000009467 reduction Effects 0.000 description 5
XODAOBAZOQSFDS-UHFFFAOYSA-N 2-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)NC(C(O)=O)=CC1=CC=CC=C1 XODAOBAZOQSFDS-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
UFDFFEMHDKXMBG-UHFFFAOYSA-N 2-acetamidoprop-2-enoic acid Chemical compound CC(=O)NC(=C)C(O)=O UFDFFEMHDKXMBG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical compound O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 3
229910052621 halloysite Inorganic materials 0.000 description 3
239000002815 homogeneous catalyst Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229920002223 polystyrene Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
239000000047 product Substances 0.000 description 2
VFUFIIXSVCSRBQ-NSHDSACASA-N (2S)-2-acetamido-3-(3-acetyloxy-4-methoxyphenyl)propanoic acid Chemical compound COC1=CC=C(C[C@H](NC(C)=O)C(O)=O)C=C1OC(C)=O VFUFIIXSVCSRBQ-NSHDSACASA-N 0.000 description 1
CBQJSKKFNMDLON-JTQLQIEISA-N N-acetyl-L-phenylalanine Chemical compound CC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 CBQJSKKFNMDLON-JTQLQIEISA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
-1 alpha-methyl-benzyl Chemical group 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
QIIDJGRNOPDQIC-UHFFFAOYSA-N cyclohexylmethyl-[(2-methoxyphenyl)methyl]phosphane;rhodium Chemical compound [Rh].COC1=CC=CC=C1CPCC1CCCCC1 QIIDJGRNOPDQIC-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
238000006459 hydrosilylation reaction Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
239000011229 interlayer Substances 0.000 description 1
HZPZCHFYBJYZKQ-UHFFFAOYSA-N n,n'-bis(diphenylphosphanyl)ethane-1,2-diamine Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)NCCNP(C=1C=CC=CC=1)C1=CC=CC=C1 HZPZCHFYBJYZKQ-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
- B01J31/1855—Triamide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1865—Phosphonites (RP(OR)2), their isomeric phosphinates (R2(RO)P=O) and RO-substitution derivatives thereof
- B01J31/187—Amide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
- B01J31/188—Amide derivatives thereof
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/60—Reduction reactions, e.g. hydrogenation
- B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
- B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
- B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/822—Rhodium
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Materials Engineering (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000311978A 1977-10-17 1978-09-25 Asymmetric hydrogenation of prochiral olefines by complexes of transition metals immobilized in clay-like minerals Expired CA1148564A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT28666A/77		1977-10-17
IT28666/77A IT1087963B (it)	1977-10-17	1977-10-17	Idrogenazione asimmetrica di olefine prochirali mediante complessi di metalli di transazione immobilizzati in minerali argillosi.

Publications (1)

Publication Number	Publication Date
CA1148564A true CA1148564A (en)	1983-06-21

Family

ID=11223981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000311978A Expired CA1148564A (en)	1977-10-17	1978-09-25	Asymmetric hydrogenation of prochiral olefines by complexes of transition metals immobilized in clay-like minerals

Country Status (20)

Country	Link
JP (1)	JPS5466615A (cs)
AU (1)	AU520574B2 (cs)
BE (1)	BE871320A (cs)
CA (1)	CA1148564A (cs)
CH (1)	CH636589A5 (cs)
CS (1)	CS208483B2 (cs)
DD (1)	DD139251A5 (cs)
DE (1)	DE2845216C2 (cs)
DK (1)	DK461478A (cs)
FR (1)	FR2405911A1 (cs)
GB (1)	GB2006770B (cs)
HU (1)	HU181953B (cs)
IL (1)	IL55733A (cs)
IT (1)	IT1087963B (cs)
LU (1)	LU80370A1 (cs)
NL (1)	NL7810236A (cs)
NO (1)	NO148778C (cs)
SE (1)	SE435923B (cs)
YU (1)	YU237578A (cs)
ZA (1)	ZA785486B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU190864B (en) *	1983-12-08	1986-11-28	Alkaloida Vegyeszeti Gyar	Process for production of phenil-alanin derivatives
GB8519008D0 (en) *	1985-07-27	1985-09-04	British Petroleum Co Plc	Chemical process

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4008281A (en) *	1973-12-03	1977-02-15	Monsanto Company	Asymmetric catalysis
CA1109074A (en) *	1976-04-26	1981-09-15	Mario Fiorini	Asymmetrical hydrogenation and related means for this purpose

1977
- 1977-10-17 IT IT28666/77A patent/IT1087963B/it active
1978
- 1978-09-25 CA CA000311978A patent/CA1148564A/en not_active Expired
- 1978-09-27 ZA ZA00785486A patent/ZA785486B/xx unknown
- 1978-09-27 AU AU40251/78A patent/AU520574B2/en not_active Expired
- 1978-10-09 JP JP12370578A patent/JPS5466615A/ja active Pending
- 1978-10-10 YU YU02375/78A patent/YU237578A/xx unknown
- 1978-10-11 GB GB7840114A patent/GB2006770B/en not_active Expired
- 1978-10-11 NL NL7810236A patent/NL7810236A/xx not_active Application Discontinuation
- 1978-10-13 IL IL55733A patent/IL55733A/xx unknown
- 1978-10-16 DD DD78208480A patent/DD139251A5/xx unknown
- 1978-10-16 CS CS786724A patent/CS208483B2/cs unknown
- 1978-10-16 SE SE7810776A patent/SE435923B/sv unknown
- 1978-10-16 CH CH1070078A patent/CH636589A5/it not_active IP Right Cessation
- 1978-10-16 DK DK461478A patent/DK461478A/da not_active Application Discontinuation
- 1978-10-16 HU HU78SA3141A patent/HU181953B/hu unknown
- 1978-10-16 NO NO783492A patent/NO148778C/no unknown
- 1978-10-16 LU LU80370A patent/LU80370A1/xx unknown
- 1978-10-16 FR FR7829446A patent/FR2405911A1/fr active Granted
- 1978-10-17 DE DE2845216A patent/DE2845216C2/de not_active Expired
- 1978-10-17 BE BE191166A patent/BE871320A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU4025178A (en)	1980-04-03
DE2845216A1 (de)	1979-04-19
DK461478A (da)	1979-04-18
IL55733A (en)	1981-11-30
NO148778C (no)	1983-12-14
JPS5466615A (en)	1979-05-29
DE2845216C2 (de)	1984-05-10
BE871320A (fr)	1979-04-17
IT1087963B (it)	1985-06-04
GB2006770A (en)	1979-05-10
NL7810236A (nl)	1979-04-19
FR2405911A1 (fr)	1979-05-11
GB2006770B (en)	1982-03-17
CH636589A5 (it)	1983-06-15
YU237578A (en)	1983-01-21
IL55733A0 (en)	1978-12-17
SE435923B (sv)	1984-10-29
AU520574B2 (en)	1982-02-11
CS208483B2 (en)	1981-09-15
LU80370A1 (fr)	1979-03-19
ZA785486B (en)	1979-09-26
SE7810776L (sv)	1979-04-18
NO783492L (no)	1979-04-18
NO148778B (no)	1983-09-05
HU181953B (en)	1983-11-28
DD139251A5 (de)	1979-12-19
FR2405911B1 (cs)	1981-03-20

Legal Events

Date	Code	Title	Description
2000-06-21	MKEX	Expiry

Publication	Publication Date	Title
US5736480A (en)	1998-04-07	Supported phase chiral sulfonated BINAP catalyst solubilized in alcohol and method of asymmetric hydrogenation
EP0938488B1 (en)	2002-01-02	Phosphine ligands
CA1051912A (en)	1979-04-03	Asymmetric catalysis
CA2275458C (en)	2006-06-06	Novel supported catalysts
Lensink et al.	1992	Improving enantioselectivity by using a mono-sulphonated diphosphine as ligand for homogeneous imine hydrogenation
Brown et al.	1991	Enantioselective catalytic transfer hydrogenation of α, β-unsaturated carboxylic acids with formates catalyzed by novel ruthenium phosphine complexes
JP2007517850A (ja)	2007-07-05	不斉変換触媒を製造するための方法
Crosman et al.	2005	Enantioselective hydrogenation over immobilized rhodium diphosphine complexes on aluminated SBA-15
WO2009023452A1 (en)	2009-02-19	Methods for making immobilized aryl-containing ligands
Cullen et al.	1987	Polymer supported ferrocene derivatives. Catalytic hydrosilylation of olefins by supported palladium and platinum complexes
CA1148564A (en)	1983-06-21	Asymmetric hydrogenation of prochiral olefines by complexes of transition metals immobilized in clay-like minerals
EP0408321B1 (en)	1993-04-14	Transition metal tris-dithiolene and related complexes as precursors to active catalysts
Orsini et al.	1989	Influence of the catalyst on the Pd0-mediated reactions of BrZnCH (CH3) COOtBu with vinyl and aryl triflates
Ferrari et al.	1992	Anchoring metal species on a thiourea-functionalized silica xerogel. In situ production of colloidal palladium particles
JP2010524661A (ja)	2010-07-22	不均一系パラジウム触媒の合成方法、得られる触媒およびこの使用
US4328364A (en)	1982-05-04	Asymmetric hydrogenation of prochiral olefins by complexes of transition metals immobilized in clay-like minerals
US4107079A (en)	1978-08-15	Insoluble metallic complexes and catalysts therefrom
US5935892A (en)	1999-08-10	Supported phase catalyst
JPH05339368A (ja)	1993-12-21	不均一系担持触媒によるオレフィン／一酸化炭素交互コポリマーの製造法
US6162951A (en)	2000-12-19	Phosphine ligands
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WO1997005150A1 (en)	1997-02-13	Iridium-diphosphine complexes and process for the hydrogenation of imines
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