WO2004112951A2 - Preparation of ruthenium-based olefin metathesis catalysts - Google Patents
Preparation of ruthenium-based olefin metathesis catalysts Download PDFInfo
- Publication number
- WO2004112951A2 WO2004112951A2 PCT/US2004/019712 US2004019712W WO2004112951A2 WO 2004112951 A2 WO2004112951 A2 WO 2004112951A2 US 2004019712 W US2004019712 W US 2004019712W WO 2004112951 A2 WO2004112951 A2 WO 2004112951A2
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- WO
- WIPO (PCT)
- Prior art keywords
- rucl
- mes
- smes
- trimethylphenyl
- bis
- Prior art date
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Classifications
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- 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
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
-
- 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
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
- B01J31/2269—Heterocyclic carbenes
- B01J31/2273—Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
-
- 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
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- 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
- B01J2531/821—Ruthenium
Definitions
- the present invention relates to olefin metathesis. More particularly, the present invention relates to synthesis of olefin metathesis catalysts.
- complex 1 has been synthesized by reaction of RuCl 2 (PPh 3 ) with diazo compound according to eq. 1.
- US Patent 6,369,265 Use of a catalyst system comprising nickel, palladium, or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in kumada coupling reactions:
- US Patent 6,362,357 Use a catalyst system comprising nickel palladium or platinum and imidazoline-2-ylidene or imidazolidine-2-ylidene in stille coupling reactions;
- the present invention includes a process for the preparation of ruthenium- based olefin metathesis catalysts.
- the inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis. Other prior art routes are described above in the Background of the Invention.
- the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis.
- the process includes providing a Ru-indenylidene complex and an excess of an olefin.
- the present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, alkoxides, aryloxides, anionic species etc.;
- PCy 3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; either of the PCy3 can be any 2-electron donor.
- the present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L 1 )Ru(L 2 )(3-phenylindenylid-l-ene)Cl 2 (where Li and L 2 can be two- electron donors) and an olefin.
- at least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
- PCy3 can be N-heterocyclcic carbene (NHC), and mixed NHC/PR combinations; in general either of the PCy can be any 2-electron donor.
- complex 1 could be synthesized via a cross metathesis reaction according to eq. 3 eliminating the need for hazardous handling of a diazo reagent.
- PCy3 can be N- heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; in general either of the PCy 3 can be any 2-electron donor.
- the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, including those mentioned above in the Background of the Invention.
- the inventor has discovered that Ru-carbene complexes can be made from the Ru-indenylidene complex by cross metathesis.
- the present invention thus includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising making Ru-carbene complexes from a Ru-indenylidene complex by cross metathesis.
- the process includes providing a Ru-indenylidene complex and an excess of an olefin.
- the present invention includes a process for the preparation of ruthenium-based olefin metathesis catalysts, comprising eq. 3 or a process similar to eq. 3, with one or more of the following variations: in place of CI one could use other halides, pseudohalides, aikoxides, aryloxides, anionic species etc.;
- PCy can be N-heterocyclcic carbene (NHC), and mixed NHC/PR 3 combinations; either of the PCy3 can be any 2-electron donor.
- the present invention includes a synthetic method leading to the isolation of ruthenium-based olefin metathesis catalysts comprising a cross metathesis reaction between (L 1 )Ru(L 2 )(3-phenylindenylid-l-ene)Cl (where Lj and L can be two- electron donors) and an olefin.
- At least one of the following ruthenium olefin metathesis catalysts is preferably isolated:
- AU measurements disclosed herein are at standard temperature and pressure, at sea level on Earth, unless indicated otherwise.
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- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04755714A EP1654060A4 (en) | 2003-06-19 | 2004-06-21 | Preparation of ruthenium-based olefin metathesis catalysts |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47977103P | 2003-06-19 | 2003-06-19 | |
US60/479,771 | 2003-06-19 |
Publications (2)
Publication Number | Publication Date |
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WO2004112951A2 true WO2004112951A2 (en) | 2004-12-29 |
WO2004112951A3 WO2004112951A3 (en) | 2005-04-21 |
Family
ID=33539218
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2004/019712 WO2004112951A2 (en) | 2003-06-19 | 2004-06-21 | Preparation of ruthenium-based olefin metathesis catalysts |
Country Status (3)
Country | Link |
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US (1) | US7205424B2 (en) |
EP (1) | EP1654060A4 (en) |
WO (1) | WO2004112951A2 (en) |
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EP2027920A1 (en) | 2007-08-21 | 2009-02-25 | Lanxess Deutschland GmbH | Catalysts for metathesis reactions |
DE102007039527A1 (en) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions |
DE102007039525A1 (en) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Process for metathesis degradation of nitrile rubber |
DE102007039526A1 (en) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | Catalyst systems and their use for metathesis reactions |
DE102007039695A1 (en) | 2007-08-22 | 2009-02-26 | Lanxess Deutschland Gmbh | New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions |
EP2145681A1 (en) | 2008-07-08 | 2010-01-20 | Lanxess Deutschland GmbH | Method for the reduction of the molecular weight of nitrile rubber |
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Cited By (30)
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EP2027920A1 (en) | 2007-08-21 | 2009-02-25 | Lanxess Deutschland GmbH | Catalysts for metathesis reactions |
DE102007039527A1 (en) | 2007-08-21 | 2009-02-26 | Lanxess Deutschland Gmbh | New ruthenium- and osmium-carbene-complex catalysts, which are bonded with chiral carbon atoms or over double bonds at a catalyst base skeleton, useful e.g. in metathesis-reactions, preferably in ring closing metathesis reactions |
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WO2004112951A3 (en) | 2005-04-21 |
EP1654060A2 (en) | 2006-05-10 |
EP1654060A4 (en) | 2007-08-08 |
US7205424B2 (en) | 2007-04-17 |
US20050026774A1 (en) | 2005-02-03 |
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