WO2011056884A3 - Complexes carbéniques de sels métalliques de lithium et/ou de magnésium et leurs utilisations - Google Patents

Complexes carbéniques de sels métalliques de lithium et/ou de magnésium et leurs utilisations 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
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WIPO (PCT)
Prior art keywords
carbene
metal
ligand
transition
carbene complexes
Prior art date
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Ceased
Application number
PCT/US2010/055313
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English (en)
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WO2011056884A2 (fr
Inventor
John R. Hagadorn
Matthew W. Holtcamp
Matthew S. Bedoya
Renuka N. Ganesh
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ExxonMobil Chemical Patents Inc
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ExxonMobil Chemical Patents Inc
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Publication of WO2011056884A2 publication Critical patent/WO2011056884A2/fr
Publication of WO2011056884A3 publication Critical patent/WO2011056884A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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

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

Abstract

Cette invention concerne un complexe carbénique de sel métallique représenté par la formule : [T-M(R)c]n. Dans cette formule, R est un groupe monoanionique; c est 1 ou 2; M est Li ou Mg; T est un ligand du type carbène cyclique; et n est choisi dans le groupe des nombres entiers allant de 1 à 24. Le complexe selon l'invention subit une décomposition de 50 % ou moins quand il est stocké dans 0,01 mole de benzène à 23°C pendant une heure. Des complexes carbéniques de métaux de transition préparés à partir des complexes carbéniques de sels métalliques selon l'invention sont également décrits, lesdits complexes carbéniques de métaux de transition étant représentés par la formule : [M*(T)(L0)q(L1-)s(L2-)t]g, où M* est un métal de transition du Groupe 6, 7, 8, 9, 10, 11 ou 12, T est un ligand du type carbène cyclique, L0 est un ligand neutre, L1- est un ligand monoanionique, L2- est un ligand dianionique, q est 0, 1, 2, 3 ou 4, s est 0, 1, 2, 3, ou 4, t est 0, 1, 2, 3, ou 4, et g est la charge globale de la molécule. Les complexes carbéniques de métaux de transition selon l'invention peuvent être utilisés pour des réactions de synthèse, dont la métathèse d'oléfines.
PCT/US2010/055313 2009-11-09 2010-11-03 Complexes carbéniques de sels métalliques de lithium et/ou de magnésium et leurs utilisations Ceased WO2011056884A2 (fr)

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 (fr) 2011-05-12
WO2011056884A3 true WO2011056884A3 (fr) 2011-09-09

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Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013158225A1 (fr) 2012-04-18 2013-10-24 Exxonmobil Chemical Patents Inc. Compositions de polyoléfine et leurs procédés de production
WO2015033313A2 (fr) * 2013-09-06 2015-03-12 Mandal Swadhin Kumar Complexes carbène-métal n-hétérocycliques anormaux, leurs synthèse et procédés
CN105693776B (zh) * 2016-03-08 2018-03-13 沈阳化工大学 笼状钌金属有机配合物晶体及其制备方法
WO2022008946A1 (fr) * 2020-07-08 2022-01-13 Centre National De La Recherche Scientifique Énantiomères optiquement purs de complexes de ruthénium et leurs utilisations

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 *

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