Title:
CATALYST COMPRISING A CHIRAL CATIONIC METAL-LIGAND COMPLEX IMMOBILISED ON A MESOPOROUS ALUMINO-SILICATE SUPPORT, ITS PREPARATION AND USE IN ASYMMETRIC HYDROGENATION
Document Type and Number:
WIPO Patent Application WO2002036261
Kind Code:
A3
Abstract:
A solid catalyst for asymmetric hydrogenation reactions is disclosed comprising a chiral cationic metal-ligand complex immobilised on a mesoporous alumino-silicate support. The catalyst is formed by ion exchange with the acid sites of the support. The catalyst is reusable, and maintains its activity after use. The metal is preferably Rh, Ir or Ru. The ligands are preferably neutral ligands selected from the group consisting of BINAP, DuPHOS, BIPHEP, TMBTP, BITIANAP, BIBFUP, bppm, CARBOPHOS, JOSIPHOS, BPE, DEGPHOS, DIOP, BIPNOR, DIPAMP, CHIRAPHOS, PROPHOS, PYPHOS, BINAPAN, SELKE or formula (I), formula (II), formula (III).
Inventors:
HEMS WILLIAM PATRICK (GB)
HUTCHINGS GRAHAM JOHN (GB)
HUTCHINGS GRAHAM JOHN (GB)
Application Number:
PCT/GB2001/004842
Publication Date:
October 31, 2002
Filing Date:
November 01, 2001
Export Citation:
Assignee:
ICI PLC (GB)
HEMS WILLIAM PATRICK (GB)
HUTCHINGS GRAHAM JOHN (GB)
HEMS WILLIAM PATRICK (GB)
HUTCHINGS GRAHAM JOHN (GB)
International Classes:
B01J29/04; B01J31/16; B01J31/18; B01J31/22; B01J31/24; C07B53/00; C07C29/145; C07C67/303; C07C231/18; C07C233/47; (IPC1-7): B01J31/16; B01J29/04; B01J35/10; B01J31/24; B01J37/30; C07B53/00; C07C5/03; C07C29/143; C07C67/303; C07C209/52
Domestic Patent References:
| WO1998028074A1 | 1998-07-02 |
Foreign References:
| DE19820411A1 | 2000-01-27 | |||
| US5252751A | 1993-10-12 | |||
| US5244857A | 1993-09-14 |
Other References:
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SAYARI A: "CATALYSIS BY CRYSTALLINE MESOPOROUS MOLECULAR SIEVES", CHEMISTRY OF MATERIALS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 8, no. 8, 1 August 1996 (1996-08-01), pages 1840 - 1852, XP000626890, ISSN: 0897-4756
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CHIN, CHONG SHIK ET AL: "Synthesis, reactions and catalytic activities of iridium complexes intercalated into montmorillonite", XP002193278, retrieved from STN Database accession no. 118:265295
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PINNAVAIA, THOMAS J. ET AL: "Intercalation of catalytically active metal complexes in mica-type silicates. Rhodium hydrogenation catalysts", XP002193279, retrieved from STN Database accession no. 92:41021
CLARK, JAMES H. ET AL.: "Catalysis of liquid phase organic reactions using chemically modified mesoporous inorganic solids", CHEMICAL COMMUNICATIONS, no. 8, 1998, GB, pages 853 - 860, XP002193275
LINDNER E ET AL: "SYNTHESIS AND CHARACTERIZATION OF POLY(ALUMOSILOXANE)-BOUND (ETHER-PHOSPHINE)RUTHENIUM(II) COMPLEXES", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 36, no. 5, 1997, pages 862 - 866, XP000997796, ISSN: 0020-1669
NOZAKI, K. ET AL.: "Hydroesterification of styrene catalyzed by Montmorillonite-Diphenylphosphinepalladium(II) chloride in the presence of chiral phosphines", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 118, no. 2, 1997, pages 247 - 253, XP002193276
DE REGE, FRANCIS M. ET AL.: "Non-covalent immobilization of homogenous cationic chiral rhodium-phosphine catalysts on silica surfaces", CHEMICAL COMMUNICATIONS, no. 18, 12 September 2000 (2000-09-12), GB, pages 1797 - 1798, XP002193277
FACHE, F. ET AL.: "Nitrogen-Containing Ligands for Asymmetric Homogenous and Heterogenous Catalysis", CHEMICAL REVIEWS, vol. 100, no. 6, 16 May 2000 (2000-05-16), pages 2159 - 2231, XP002201872
LANGER T ET AL: "Highly Efficient New Catalysts for Enantioselective Transfer Hydrogenation of Ketones", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 37, no. 9, 26 February 1996 (1996-02-26), pages 1381 - 1384, XP004030049, ISSN: 0040-4039
ANSON M S ET AL: "Palladium Catalysed Heck and Enantioselective Allylic Substitution Reactions Using Reverse Phase Silica Supports", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 40, no. 39, 24 September 1999 (1999-09-24), pages 7147 - 7150, XP004177220, ISSN: 0040-4039
SAYARI A: "CATALYSIS BY CRYSTALLINE MESOPOROUS MOLECULAR SIEVES", CHEMISTRY OF MATERIALS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 8, no. 8, 1 August 1996 (1996-08-01), pages 1840 - 1852, XP000626890, ISSN: 0897-4756
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CHIN, CHONG SHIK ET AL: "Synthesis, reactions and catalytic activities of iridium complexes intercalated into montmorillonite", XP002193278, retrieved from STN Database accession no. 118:265295
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PINNAVAIA, THOMAS J. ET AL: "Intercalation of catalytically active metal complexes in mica-type silicates. Rhodium hydrogenation catalysts", XP002193279, retrieved from STN Database accession no. 92:41021
CLARK, JAMES H. ET AL.: "Catalysis of liquid phase organic reactions using chemically modified mesoporous inorganic solids", CHEMICAL COMMUNICATIONS, no. 8, 1998, GB, pages 853 - 860, XP002193275
LINDNER E ET AL: "SYNTHESIS AND CHARACTERIZATION OF POLY(ALUMOSILOXANE)-BOUND (ETHER-PHOSPHINE)RUTHENIUM(II) COMPLEXES", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 36, no. 5, 1997, pages 862 - 866, XP000997796, ISSN: 0020-1669
NOZAKI, K. ET AL.: "Hydroesterification of styrene catalyzed by Montmorillonite-Diphenylphosphinepalladium(II) chloride in the presence of chiral phosphines", JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 118, no. 2, 1997, pages 247 - 253, XP002193276
DE REGE, FRANCIS M. ET AL.: "Non-covalent immobilization of homogenous cationic chiral rhodium-phosphine catalysts on silica surfaces", CHEMICAL COMMUNICATIONS, no. 18, 12 September 2000 (2000-09-12), GB, pages 1797 - 1798, XP002193277
FACHE, F. ET AL.: "Nitrogen-Containing Ligands for Asymmetric Homogenous and Heterogenous Catalysis", CHEMICAL REVIEWS, vol. 100, no. 6, 16 May 2000 (2000-05-16), pages 2159 - 2231, XP002201872
LANGER T ET AL: "Highly Efficient New Catalysts for Enantioselective Transfer Hydrogenation of Ketones", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 37, no. 9, 26 February 1996 (1996-02-26), pages 1381 - 1384, XP004030049, ISSN: 0040-4039
ANSON M S ET AL: "Palladium Catalysed Heck and Enantioselective Allylic Substitution Reactions Using Reverse Phase Silica Supports", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 40, no. 39, 24 September 1999 (1999-09-24), pages 7147 - 7150, XP004177220, ISSN: 0040-4039
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