AU2012206966B2 - Z-selective olefin metathesis catalysts and their synthetic procedure - Google Patents

Z-selective olefin metathesis catalysts and their synthetic procedure Download PDF

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Publication number
AU2012206966B2
AU2012206966B2 AU2012206966A AU2012206966A AU2012206966B2 AU 2012206966 B2 AU2012206966 B2 AU 2012206966B2 AU 2012206966 A AU2012206966 A AU 2012206966A AU 2012206966 A AU2012206966 A AU 2012206966A AU 2012206966 B2 AU2012206966 B2 AU 2012206966B2
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substituted
heteroatom
aryl
hydrocarbyl
compound
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AU2012206966A1 (en
Inventor
Koji Endo
Robert Howard Grubbs
Myles Benton HERBERT
Benjamin Keith KEITZ
Paresma Rasiklal PATEL
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California Institute of Technology
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California Institute of Technology
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    • 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
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • 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
    • 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
    • C07C67/343—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 by increase in the number of carbon atoms
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • 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
    • 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
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • 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
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

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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)
AU2012206966A 2011-01-14 2012-01-17 Z-selective olefin metathesis catalysts and their synthetic procedure Ceased AU2012206966B2 (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201161432849P 2011-01-14 2011-01-14
US61/432,849 2011-01-14
US201161433949P 2011-01-18 2011-01-18
US61/433,949 2011-01-18
US201161515262P 2011-08-04 2011-08-04
US61/515,262 2011-08-04
PCT/US2012/021609 WO2012097379A2 (en) 2011-01-14 2012-01-17 Z-selective olefin metathesis catalysts and their synthetic procedure

Publications (2)

Publication Number Publication Date
AU2012206966A1 AU2012206966A1 (en) 2013-08-08
AU2012206966B2 true AU2012206966B2 (en) 2016-11-17

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AU2012206966A Ceased AU2012206966B2 (en) 2011-01-14 2012-01-17 Z-selective olefin metathesis catalysts and their synthetic procedure

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US (1) US9597674B2 (enExample)
EP (1) EP2663398B1 (enExample)
JP (1) JP5893646B2 (enExample)
KR (1) KR101835170B1 (enExample)
CN (1) CN103402628B (enExample)
AU (1) AU2012206966B2 (enExample)
BR (1) BR112013017938B1 (enExample)
CA (1) CA2824518C (enExample)
IL (1) IL227432A (enExample)
PL (1) PL2663398T3 (enExample)
SG (1) SG191980A1 (enExample)
WO (1) WO2012097379A2 (enExample)
ZA (2) ZA201305726B (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013134192A1 (en) 2012-03-05 2013-09-12 California Institute Of Technology Syntheses of z-olefin-containing lepidopteran insect pheromones
EP2867243B1 (en) 2012-06-29 2016-04-13 Apeiron Synthesis S.A. Metal complexes, their application and methods of carrying out of metathesis reaction
WO2014022482A1 (en) 2012-08-01 2014-02-06 California Institute Of Technology Solvent-free enyne metathesis polymerization
US9234985B2 (en) 2012-08-01 2016-01-12 California Institute Of Technology Birefringent polymer brush structures formed by surface initiated ring-opening metathesis polymerization
WO2014093687A1 (en) * 2012-12-12 2014-06-19 California Institute Of Technology Z-selective metathesis catalysts
ES2699416T3 (es) * 2013-04-09 2019-02-11 Materia Inc Preparación de tensioactivos mediante metátesis cruzada
US9758445B2 (en) 2013-04-09 2017-09-12 Materia, Inc. Preparation of surfactants via cross-metathesis
US9663440B2 (en) 2013-04-09 2017-05-30 Materia, Inc. Cross metathesis of poly-branched poly-olefins
WO2014186631A1 (en) * 2013-05-15 2014-11-20 California Institute Of Technology Highly z-selective and enantioselective ring opening/cross metathesis
US9938253B2 (en) 2013-06-12 2018-04-10 Trustees Of Boston College Catalysts for efficient Z-selective metathesis
WO2016014954A1 (en) * 2014-07-25 2016-01-28 California Institute Of Technology Tandem z-selective metathesis / dihydroxylation
CA2999864A1 (en) * 2015-09-24 2017-03-30 Materia, Inc. Metal carbene olefin metathesis catalysts
CA3006976A1 (en) 2015-12-10 2017-06-15 California Institute Of Technology Olefin metathesis catalysts
CN114106057B (zh) * 2016-10-19 2023-06-23 优美科股份公司及两合公司 Ru亚烷基络合物的合成与表征
US10320390B1 (en) 2016-11-17 2019-06-11 X Development Llc Field programmable gate array including coupled lookup tables
EP3630741A1 (en) 2017-05-30 2020-04-08 Verbio Vereinigte Bioenergie AG Methods of making olefinic e- and z-isomers
RU2020133186A (ru) * 2018-03-09 2022-04-12 Ппг Индастриз Огайо, Инк. Составы для координирования с металлом, композиции, содержащие такие составы, и способы катализирования реакций
WO2019222244A1 (en) * 2018-05-15 2019-11-21 California Institute Of Technology Total synthesis of prostaglandin j natural products by stereoretentive metathesis
US11939410B2 (en) * 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
WO2021011221A1 (en) * 2019-07-17 2021-01-21 California Institute Of Technology New syntheses of z-selective olefin metathesis catalysts
MX2022008954A (es) * 2020-03-05 2022-08-15 Firmenich & Cie Proceso para preparar un compuesto intermediario perfumante.
CN115298191A (zh) * 2020-03-13 2022-11-04 伊利诺伊大学评议会 催化氢化硅烷化的方法
CN114478166B (zh) * 2020-10-26 2024-09-27 中国石油天然气股份有限公司 一种制备端烯烃的方法
CN118056617B (zh) * 2022-11-15 2026-06-23 中国石油天然气股份有限公司 一种用于1-己烯自歧化的负载型催化剂及其制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5312940A (en) 1992-04-03 1994-05-17 California Institute Of Technology Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
US6284852B1 (en) * 1997-10-30 2001-09-04 California Institute Of Technology Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
WO2002014376A2 (en) 2000-08-10 2002-02-21 Trustees Of Boston College Recyclable metathesis catalysts
EP1455937B1 (en) 2001-11-15 2018-04-11 Materia, Inc. Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
CN1659172B (zh) * 2002-04-05 2012-08-01 加州理工学院 直接被吸电子基团取代的烯烃使用过渡金属卡宾催化剂的交叉-易位
JP5081620B2 (ja) * 2004-06-09 2012-11-28 ユーティーアイ リミテッド パートナーシップ オレフィン複分解反応の触媒としてのカチオン性置換基を含む遷移金属カルベン錯体
FR2878246B1 (fr) 2004-11-23 2007-03-30 Inst Francais Du Petrole Procede de co-production d'olefines et d'esters par ethenolyse de corps gras insatures dans des liquides ioniques non-aqueux
JP5406525B2 (ja) * 2005-07-04 2014-02-05 ツァナン・サイテック・カンパニー・リミテッド ルテニウム錯体配位子、ルテニウム錯体、固定化ルテニウム錯体触媒及びその調製方法と用途
US8877936B2 (en) * 2008-04-09 2014-11-04 California Institute Of Technology Ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene ligands with substituted backbone
EP2255877B1 (en) 2009-05-07 2014-09-24 Umicore AG & Co. KG Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Ritter, T. et al., (2006) "Rate Acceleration in Olefin Metathesis through a Fluorine-Ruthenium Interaction", JACS, vol. 128, pp 11768-11769. *
WEN, T.B. et al., (2003) "Coupling Reaction of Phenylacetylene with OsHn(PPh3)(2,6-(PPh2CH2)2C6H3) (n= 1,3)", Organometallics, vol. 22, pp 4947-4951 *
WEN, T.B. et al., (2006) "Osmium-Mediated Hexamerization of Phenylacetylene", Angew. Chem. Int. Ed., vol. 45, pp 5842-5846 *

Also Published As

Publication number Publication date
CN103402628B (zh) 2015-12-23
IL227432A0 (en) 2013-09-30
US20140106960A1 (en) 2014-04-17
IL227432A (en) 2017-12-31
CA2824518A1 (en) 2012-07-19
BR112013017938B1 (pt) 2019-10-15
EP2663398A4 (en) 2014-07-23
BR112013017938A2 (pt) 2018-11-27
JP2014503356A (ja) 2014-02-13
CA2824518C (en) 2019-03-26
EP2663398A2 (en) 2013-11-20
ZA201408071B (en) 2019-06-26
KR101835170B1 (ko) 2018-03-06
EP2663398B1 (en) 2018-07-18
KR20140021995A (ko) 2014-02-21
JP5893646B2 (ja) 2016-03-23
WO2012097379A3 (en) 2012-10-11
ZA201305726B (en) 2018-12-19
PL2663398T3 (pl) 2019-01-31
CN103402628A (zh) 2013-11-20
US9597674B2 (en) 2017-03-21
WO2012097379A2 (en) 2012-07-19
SG191980A1 (en) 2013-08-30

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