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EP2632929A4 - N-heterocyclic carbene complexes, their preparation and use - Google Patents

N-heterocyclic carbene complexes, their preparation and use

Info

Publication number
EP2632929A4
EP2632929A4 EP11835725.0A EP11835725A EP2632929A4 EP 2632929 A4 EP2632929 A4 EP 2632929A4 EP 11835725 A EP11835725 A EP 11835725A EP 2632929 A4 EP2632929 A4 EP 2632929A4
Authority
EP
European Patent Office
Prior art keywords
preparation
heterocyclic carbene
carbene complexes
complexes
heterocyclic
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.)
Withdrawn
Application number
EP11835725.0A
Other languages
German (de)
French (fr)
Other versions
EP2632929A1 (en
Inventor
A Stephen K Hashmi
Christian Lothschuetz
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.)
BASF Schweiz AG
BASF SE
Original Assignee
BASF Schweiz AG
BASF SE
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.)
Filing date
Publication date
Application filed by BASF Schweiz AG, BASF SE filed Critical BASF Schweiz AG
Priority to EP11835725.0A priority Critical patent/EP2632929A4/en
Publication of EP2632929A1 publication Critical patent/EP2632929A1/en
Publication of EP2632929A4 publication Critical patent/EP2632929A4/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07F15/006—Palladium 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
    • 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
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • 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
    • C07F15/0086—Platinum 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4233—Kumada-type, i.e. RY + R'MgZ, in which Ris optionally substituted alkyl, alkenyl, aryl, Y is the leaving group and Z is halide
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4255—Stille-type, i.e. RY + R'3SnR'', in which R is alkenyl, aryl, R' is alkyl and R'' is alkenyl or aryl
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4261—Heck-type, i.e. RY + C=C, in which R is aryl
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4266—Sonogashira-type, i.e. RY + HC-CR' triple bonds, in which R=aryl, alkenyl, alkyl and R'=H, alkyl or aryl
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
    • 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
    • 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
    • B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
    • B01J2531/18—Gold
    • 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
    • B01J2531/824—Palladium
    • 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
    • B01J2531/828—Platinum

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Catalysts (AREA)
EP11835725.0A 2010-10-28 2011-10-27 N-heterocyclic carbene complexes, their preparation and use Withdrawn EP2632929A4 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP11835725.0A EP2632929A4 (en) 2010-10-28 2011-10-27 N-heterocyclic carbene complexes, their preparation and use

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP10189282 2010-10-28
PCT/IB2011/054795 WO2012056419A1 (en) 2010-10-28 2011-10-27 N-heterocyclic carbene complexes, their preparation and use
EP11835725.0A EP2632929A4 (en) 2010-10-28 2011-10-27 N-heterocyclic carbene complexes, their preparation and use

Publications (2)

Publication Number Publication Date
EP2632929A1 EP2632929A1 (en) 2013-09-04
EP2632929A4 true EP2632929A4 (en) 2014-03-26

Family

ID=45993235

Family Applications (1)

Application Number Title Priority Date Filing Date
EP11835725.0A Withdrawn EP2632929A4 (en) 2010-10-28 2011-10-27 N-heterocyclic carbene complexes, their preparation and use

Country Status (5)

Country Link
EP (1) EP2632929A4 (en)
JP (1) JP2013542219A (en)
CN (1) CN103180332A (en)
CA (1) CA2815543A1 (en)
WO (1) WO2012056419A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2821409A1 (en) * 2013-07-05 2015-01-07 Centre National de la Recherche Scientifique (CNRS) Metal alkylidene complexes comprising an unsymmetrical unsaturated NHC ligand
CN105327713B (en) * 2015-11-16 2017-06-16 湖北大学 A kind of adamantane support NHC Pd catalyst and its production and use
US20200115389A1 (en) 2018-09-18 2020-04-16 Nikang Therapeutics, Inc. Fused tricyclic ring derivatives as src homology-2 phosphatase inhibitors
CN110449152B (en) * 2019-08-01 2022-05-10 安徽师范大学 Catalytic synthesis of triazine compounds or pyrimidine compounds using gold@cerium oxide core-shell nanomaterials
CN111116423A (en) * 2019-12-30 2020-05-08 苏州百灵威超精细材料有限公司 Process method for preparing tert-butyl isocyano
CN116858908B (en) * 2023-07-10 2025-12-05 华东师范大学 A highly stable carbene-alkynyl probe molecule self-assembly interface, its preparation method and application
CN119552198A (en) * 2024-07-10 2025-03-04 武汉大学 Application of a novel photoactive iron-nitrogen heterocyclic carbene series compounds as photoacoustic contrast agents

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000046256A1 (en) * 1999-02-05 2000-08-10 Advanced Polymer Technologies, Inc. Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1654064A2 (en) * 2003-08-11 2006-05-10 MERCK PATENT GmbH Immobilised imidazoles and ruthenium catalysts
US8299263B2 (en) * 2008-07-30 2012-10-30 University Of Southern California N-heterocyclic carbene-amido palladium(II) catalysts and method of use thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000046256A1 (en) * 1999-02-05 2000-08-10 Advanced Polymer Technologies, Inc. Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
DRAGUTAN ET AL LEVASON BILL ET AL: "NHC-Ru complexes-Friendly catalytic tools for manifold chemical transformations", COORDINATION CHEMISTRY REVIEWS, ELSEVIER SCIENCE, AMSTERDAM, NL, vol. 251, no. 5-6, 8 February 2007 (2007-02-08), pages 765 - 794, XP005880044, ISSN: 0010-8545, DOI: 10.1016/J.CCR.2006.09.002 *
FEHLHAMMER ET AL.: "Homoleptic Carbene Complexes", ZEITSCHRIFT FÜR NATURFORSCHUNG, B CHEMICAL SCIENCES, vol. 47b, 1992, pages 79 - 89, XP009176210 *
FREY G D ET AL: "A straight forward in situ preparation of NHC-substituted phosphapalladacycles", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 691, no. 11, 15 May 2006 (2006-05-15), pages 2403 - 2408, XP028047556, ISSN: 0022-328X, [retrieved on 20060515], DOI: 10.1016/J.JORGANCHEM.2006.01.018 *
LAURE BENHAMOU ET AL: "Facile Derivatization of a "Chemo-active" NHC Incorporating an Enolate Backbone and Relevant Tuning of Its Electronic Properties", ORGANOMETALLICS, vol. 29, no. 11, 14 June 2010 (2010-06-14), pages 2616 - 2630, XP055102278, ISSN: 0276-7333, DOI: 10.1021/om1003607 *
See also references of WO2012056419A1 *
VIVEK POLSHETTIWAR ET AL: "Olefin Ring Closing Metathesis and Hydrosilylation Reaction in Aqueous Medium by Grubbs Second Generation Ruthenium Catalyst", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 18, 19 September 2008 (2008-09-19), pages 7417 - 7419, XP055102068, ISSN: 0022-3263, DOI: 10.1021/jo801330c *

Also Published As

Publication number Publication date
CN103180332A (en) 2013-06-26
WO2012056419A1 (en) 2012-05-03
EP2632929A1 (en) 2013-09-04
CA2815543A1 (en) 2012-05-03
JP2013542219A (en) 2013-11-21

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