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WO2006018161A3 - Am zentralatom substituierte, immobilisierbare ruthenium(ii)-katalysatoren, verfahren zu deren herstellung und verwendung - Google Patents

Am zentralatom substituierte, immobilisierbare ruthenium(ii)-katalysatoren, verfahren zu deren herstellung und verwendung Download PDF

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Publication number
WO2006018161A3
WO2006018161A3 PCT/EP2005/008526 EP2005008526W WO2006018161A3 WO 2006018161 A3 WO2006018161 A3 WO 2006018161A3 EP 2005008526 W EP2005008526 W EP 2005008526W WO 2006018161 A3 WO2006018161 A3 WO 2006018161A3
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WO
WIPO (PCT)
Prior art keywords
catalysts
metathesis
ruthenium
production
immobilizable
Prior art date
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.)
Ceased
Application number
PCT/EP2005/008526
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English (en)
French (fr)
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WO2006018161A2 (de
Inventor
Katrin Koehler
Kati Vehlow
Siegfried Blechert
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Merck Patent GmbH
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Merck Patent GmbH
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Publication date
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Publication of WO2006018161A2 publication Critical patent/WO2006018161A2/de
Publication of WO2006018161A3 publication Critical patent/WO2006018161A3/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • 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
    • B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
    • 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
    • B01J31/1625—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups
    • B01J31/1633—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups covalent linkages via silicon containing groups
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • B01J37/0201—Impregnation
    • B01J37/0209—Impregnation involving a reaction between the support and a fluid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • 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
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • 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
    • B01J2231/52—Isomerisation reactions
    • 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
    • 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
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Die Erfindung betrifft immobilisierbare Ruthenium(II)-Katalysatoren der allgemeinen Formeln (I) und (II), die eine SiR'n(OR')3-n tragende Gruppe an mindestens einem der beiden Anionen enthalten. Die Erfindung betrifft weiterhin ein Verfahren zu deren Herstellung und die Verwendung der Verbindungen in einem Verfahren zur Herstellung von auf anorganischen Oxid-Trägern immobilisierten Ruthenium(II)-Katalysatoren der allgemeinen Formeln (Ia) und (IIa). Gegenstand der Erfindung ist auch die Verwendung der Verbindungen der allgemeinen Formeln (I), (la), (II) und (IIa) als Katalysatoren in der organischen und metallorganischen Synthese. Sie können als Katalysatoren in C-C-Kupplungsreaktionen, Hydrierungen, Isomerisierungen, Silylierungen und Hydroformylierungen eingesetzt werden. Insbesondere dienen sie als Katalysatoren in Olefinmetathesereaktionen, wie der Kreuzmetathese (CM), Ringschlussmetathese (RCM), Ringöffnungsmetathese (ROM), Ringöffnungsmetathese-Polymerisation (ROMP), azyklische Dienmetathese-Polymerisation (ADMET) und En-In-Metathese oder in einer Kombination verschiedenartiger Metathesereaktionen.
PCT/EP2005/008526 2004-08-13 2005-08-05 Am zentralatom substituierte, immobilisierbare ruthenium(ii)-katalysatoren, verfahren zu deren herstellung und verwendung Ceased WO2006018161A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004039277A DE102004039277A1 (de) 2004-08-13 2004-08-13 Am Zentralatom substituierte, immoblisierbare Ruthenium(II)-Katalysatoren, Verfahren zu deren Herstellung und Verwendung
DE102004039277.3 2004-08-13

Publications (2)

Publication Number Publication Date
WO2006018161A2 WO2006018161A2 (de) 2006-02-23
WO2006018161A3 true WO2006018161A3 (de) 2006-07-13

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PCT/EP2005/008526 Ceased WO2006018161A2 (de) 2004-08-13 2005-08-05 Am zentralatom substituierte, immobilisierbare ruthenium(ii)-katalysatoren, verfahren zu deren herstellung und verwendung

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DE (1) DE102004039277A1 (de)
WO (1) WO2006018161A2 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2904243B1 (fr) * 2006-07-31 2008-10-31 Inst Francais Du Petrole Catalyseur a base d'un support hybride organique - inorganique et son utilisation en hydroraffinage et hydroconversion
WO2008031889A2 (de) * 2006-09-15 2008-03-20 Basf Se Pnicogenhaltige pseudochelatliganden
EP2082804B1 (de) 2008-01-25 2012-10-03 Universite Claude Bernard Lyon 1 Organisch-anorganische Hybridmaterialien mit stabilisiertem Carben
US20120289617A1 (en) * 2011-05-10 2012-11-15 Saudi Arabian Oil Company Hybrid Catalyst for Olefin Metathesis
CN102351907B (zh) * 2011-08-22 2014-07-09 浙江大学 一种合成金属氮杂环卡宾配合物的方法
US9828347B2 (en) 2014-10-09 2017-11-28 The United States Of America As Represented By The Secretary Of The Air Force Backfunctionalized imidazolinium salts and NHC carbene-metal complexes
US11094997B2 (en) 2017-05-29 2021-08-17 Sumitomo Chemical Company, Limited Nonaqueous electrolyte secondary battery

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003062253A1 (en) * 2002-01-22 2003-07-31 Universiteit Gent Metal complexes for use in metathesis

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003062253A1 (en) * 2002-01-22 2003-07-31 Universiteit Gent Metal complexes for use in metathesis

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
ASTRUC D: "The metathesis reactions: from a historical perspective to recent developments", NEW JOURNAL OF CHEMISTRY, vol. 29, no. 1, 21 December 2004 (2004-12-21), XP002372866 *
BUCHMEISER M R ET AL: "Ring-opening metathesis polymerization for the preparation of surface-grafted polymer supports", MACROMOLECULES, ACS, WASHINGTON, DC, US, vol. 33, 2000, pages 32 - 39, XP002324916, ISSN: 0024-9297 *
BUCHMEISER M R: "Recent advances in the synthesis of supported metathesis catalysts", NEW JOURNAL OF CHEMISTRY, vol. 28, no. 5, 8 April 2004 (2004-04-08), pages 549 - 557, XP002372864 *
CLERCQ B D ET AL: "Immobilization of multifunctional Schiff base containing ruthenium complexes on MCM-41", APPLIED CATALYSIS A: GENERAL, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 247, no. 2, 25 July 2003 (2003-07-25), pages 345 - 364, XP004440496, ISSN: 0926-860X *
DROZDZAK ET AL: "Ruthenium complexes bearing bidentate Schiff base ligands as efficient catalysts for organic and polymer syntheses", COORDINATION CHEMISTRY REVIEWS, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 249, no. 24, 6 June 2005 (2005-06-06), pages 3055 - 3074, XP005174429, ISSN: 0010-8545 *
FUERSTNER A: "OLEFIN METATHESIS AND BEYOND", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, WILEY VCH VERLAG, WEINHEIM, DE, vol. 39, 2000, pages 3012 - 3043, XP002957487, ISSN: 1433-7851 *
GESSLER S ET AL: "Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 41, no. 51, 16 December 2000 (2000-12-16), pages 9973 - 9976, XP004225200, ISSN: 0040-4039 *
HARRITY ET AL: "Chromenes through Metal-Catalyzed Reactions of Styrenyl Ethers. Mechanism and Utility in Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 120, 18 March 1998 (1998-03-18), pages 2343 - 2351, XP002083201, ISSN: 0002-7863 *
KINGSBURY J S ET AL: "A RECYCLABLE RU-BASED METATHESIS CATALYST", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 121, no. 4, 3 February 1999 (1999-02-03), pages 791 - 799, XP002906691, ISSN: 0002-7863 *
KRAUSE J O ET AL: "Monolith- and Silica-Supported Carboxylate-Based Grubbs-Herrmann-Type Metathesis Catalysts", ADVANCED SYNTHESIS & CATALYSIS, vol. 345, no. 8, 7 August 2003 (2003-08-07), pages 996 - 1004, XP002372865 *

Also Published As

Publication number Publication date
WO2006018161A2 (de) 2006-02-23
DE102004039277A1 (de) 2006-02-23

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