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WO2011059803A3 - Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis - Google Patents

Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis Download PDF

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Publication number
WO2011059803A3
WO2011059803A3 PCT/US2010/054661 US2010054661W WO2011059803A3 WO 2011059803 A3 WO2011059803 A3 WO 2011059803A3 US 2010054661 W US2010054661 W US 2010054661W WO 2011059803 A3 WO2011059803 A3 WO 2011059803A3
Authority
WO
WIPO (PCT)
Prior art keywords
ruthenium
olefin
alkylidenes
ratios
core
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/US2010/054661
Other languages
French (fr)
Other versions
WO2011059803A2 (en
Inventor
Christopher W. Bielawski
Evelyn Rosen
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.)
University of Texas System
University of Texas at Austin
Original Assignee
University of Texas System
University of Texas at Austin
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 University of Texas System, University of Texas at Austin filed Critical University of Texas System
Publication of WO2011059803A2 publication Critical patent/WO2011059803A2/en
Publication of WO2011059803A3 publication Critical patent/WO2011059803A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • 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)
    • B01J31/2278—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • 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
    • B01J2231/50—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
    • 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
    • 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
    • C07C2531/24—Phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

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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)
  • Catalysts (AREA)

Abstract

According to one embodiment, the disclosure provides a ruthenium (Ru)-based olefin metathesis reaction catalyst containing a core including a ruthenium-based alkylidene and at least one acyclic diaminocarbene (ADC) ligand covalently bound to the core. The disclosure also provides a method of catalyzing an olefin metathesis reaction by reacting a first olefin and a second olefin in the presence of a ruthenium (Ru)-based olefin metathesis reaction catalyst comprising a core comprising a ruthenium-based alkylidene and at least one acyclic diaminocarbene (ADC) ligand covalently bound to the core to synthesize a third olefin mixture. Finally, the disclosure further provides methods of preparing ruthenium (Ru)-based catalysts.
PCT/US2010/054661 2009-10-29 2010-10-29 Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis Ceased WO2011059803A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US25610809P 2009-10-29 2009-10-29
US61/256,108 2009-10-29
US34813210P 2010-05-25 2010-05-25
US61/348,132 2010-05-25

Publications (2)

Publication Number Publication Date
WO2011059803A2 WO2011059803A2 (en) 2011-05-19
WO2011059803A3 true WO2011059803A3 (en) 2011-11-17

Family

ID=43992322

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/054661 Ceased WO2011059803A2 (en) 2009-10-29 2010-10-29 Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis

Country Status (1)

Country Link
WO (1) WO2011059803A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113000066B (en) * 2021-01-09 2022-04-12 河南大学 A kind of Z-selective ruthenium carbene olefin metathesis catalyst and its preparation method and application

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030055262A1 (en) * 2001-04-16 2003-03-20 Grubbs Robert H. Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts
US20030119660A1 (en) * 2001-10-02 2003-06-26 Herrmann Wolfgang A. Novel transition metal complexes with diaminocarbene ligands and their use in reactions catalyzed by transition metals
US20030195357A1 (en) * 2000-08-11 2003-10-16 Wolfram Stuer Ruthenium complexes containing carboids
US20040095792A1 (en) * 1998-04-06 2004-05-20 Herrmann Wolfgang Anton Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040095792A1 (en) * 1998-04-06 2004-05-20 Herrmann Wolfgang Anton Alkylidene complexes of ruthenium containing N-heterocyclic carbene ligands; use as highly active, selective catalysts for olefin metathesis
US20030195357A1 (en) * 2000-08-11 2003-10-16 Wolfram Stuer Ruthenium complexes containing carboids
US20030055262A1 (en) * 2001-04-16 2003-03-20 Grubbs Robert H. Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts
US20030119660A1 (en) * 2001-10-02 2003-06-26 Herrmann Wolfgang A. Novel transition metal complexes with diaminocarbene ligands and their use in reactions catalyzed by transition metals

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHRISTOPHER W. BIELAWSKI ET AL., ORGANOMETALLICS, vol. 29, 6 November 2009 (2009-11-06), pages 250 - 256 *

Also Published As

Publication number Publication date
WO2011059803A2 (en) 2011-05-19

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