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WO2011056884A3 - Carbene complexes of lithium and/or magnesium metal salts, and uses thereof - Google Patents

Carbene complexes of lithium and/or magnesium metal salts, and uses thereof Download PDF

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Publication number
WO2011056884A3
WO2011056884A3 PCT/US2010/055313 US2010055313W WO2011056884A3 WO 2011056884 A3 WO2011056884 A3 WO 2011056884A3 US 2010055313 W US2010055313 W US 2010055313W WO 2011056884 A3 WO2011056884 A3 WO 2011056884A3
Authority
WO
WIPO (PCT)
Prior art keywords
carbene
metal
ligand
transition
carbene complexes
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/US2010/055313
Other languages
French (fr)
Other versions
WO2011056884A2 (en
Inventor
John R. Hagadorn
Matthew W. Holtcamp
Matthew S. Bedoya
Renuka N. Ganesh
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.)
ExxonMobil Chemical Patents Inc
Original Assignee
ExxonMobil Chemical Patents Inc
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 ExxonMobil Chemical Patents Inc filed Critical ExxonMobil Chemical Patents Inc
Publication of WO2011056884A2 publication Critical patent/WO2011056884A2/en
Publication of WO2011056884A3 publication Critical patent/WO2011056884A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07F15/0046—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
    • 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
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2265—Carbenes or carbynes, i.e.(image)
    • B01J31/2278—Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • B01J2531/11—Lithium
    • 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
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/22—Magnesium
    • 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
    • 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
    • C07C2531/22—Organic complexes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)

Abstract

This invention relates to a carbene complex of metal salt represented by the formula: [T-M(R)c]n wherein, R is a monoanionic group; c is 1 or 2; M is a Li or Mg; T is a cyclic carbene ligand; and n is selected from the group of integers comprising 1 to 24 wherein the complex has 50% or less decomposition when stored in 0.01 molar benzene at 23°C for a period of 1 hour. This invention also relates to transition-metal-carbene complexes prepared from such carbene complexes of metal salts, where the transition-metal-carbene complex is represented by the formula: [M*(T)(L0)q(L1-)s(L2-)t]g, where M* is a transition metal from Group 6, 7, 8, 9, 10, 11 or 12, T is a cyclic carbene ligand, L0 is a neutral ligand, L1- is a monoanionic ligand, L2- is a dianionic ligand, q is 0, 1, 2, 3 or 4, s is 0, 1, 2, 3, or 4, t is 0, 1, 2, 3,or 4, g is the overall charge of the molecule. The transition-metal-carbene complexes may be used for synthesis reactions, including metathesis of olefins.
PCT/US2010/055313 2009-11-09 2010-11-03 Carbene complexes of lithium and/or magnesium metal salts, and uses thereof Ceased WO2011056884A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25952109P 2009-11-09 2009-11-09
US61/259,521 2009-11-09

Publications (2)

Publication Number Publication Date
WO2011056884A2 WO2011056884A2 (en) 2011-05-12
WO2011056884A3 true WO2011056884A3 (en) 2011-09-09

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/055313 Ceased WO2011056884A2 (en) 2009-11-09 2010-11-03 Carbene complexes of lithium and/or magnesium metal salts, and uses thereof

Country Status (1)

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WO (1) WO2011056884A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013158225A1 (en) 2012-04-18 2013-10-24 Exxonmobil Chemical Patents Inc. Polyolefin compositions and methods of production thereof
WO2015033313A2 (en) * 2013-09-06 2015-03-12 Mandal Swadhin Kumar Abnormal n-heterocyclic carbene metal complexes, synthesis and processes thereof
CN105693776B (en) * 2016-03-08 2018-03-13 沈阳化工大学 Caged ruthenium Function for Organometallic Complex Crystals and preparation method thereof
WO2022008946A1 (en) * 2020-07-08 2022-01-13 Centre National De La Recherche Scientifique Optically pure enantiomers of ruthenium complexes and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7312331B2 (en) * 2005-06-17 2007-12-25 The Regents Of The University Of California Stable cyclic (alkyl)(amino) carbenes as ligands for transition metal catalysts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7312331B2 (en) * 2005-06-17 2007-12-25 The Regents Of The University Of California Stable cyclic (alkyl)(amino) carbenes as ligands for transition metal catalysts

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
F. EKKEHARDT ET AL.: "Heterocyclic Carbenes: Synthesis and Coordination Chemistry", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 17, 14 April 2008 (2008-04-14), pages 3122 - 3172 *
PIERRE DE FREMONT ET AL.: "Cationic NHC-gold(I) complexes: Synthesis, isolation, and catalytic activity", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 694, 2009, pages 551 - 560, XP025923532, DOI: doi:10.1016/j.jorganchem.2008.10.047 *
POLLY L. ARNOLD ET AL.: "Anionic Amido N-Heterocyclic Carbenes:Synthesis of Covalently Tethered Lanthanide-Carbene Complexes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 42, no. 48, 2003, pages 5981 - 5984 *
POLLY L. ARNOLD ET AL.: "Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes; crystallographic characterisation and Lewis acid catalysis", CHEMICAL COMMUNICATIONS, no. 14, 2004, pages 1612 - 1613 *
ROBERT FRAENKEL ET AL.: "A Homoleptic Carbene-Lithium Complex", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 40, no. 10, 18 May 2001 (2001-05-18), pages 1907 - 1910 *

Also Published As

Publication number Publication date
WO2011056884A2 (en) 2011-05-12

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