CA2875956C - Ruthenium complexes comprising chelating alkylidene ligands and their use as metathesis catalysts - Google Patents

Ruthenium complexes comprising chelating alkylidene ligands and their use as metathesis catalysts Download PDF

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CA2875956C
CA2875956C CA2875956A CA2875956A CA2875956C CA 2875956 C CA2875956 C CA 2875956C CA 2875956 A CA2875956 A CA 2875956A CA 2875956 A CA2875956 A CA 2875956A CA 2875956 C CA2875956 C CA 2875956C
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process according
catalyst
alkyl
complex
metathesis
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CA2875956A1 (en
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Krzysztof Skowerski
Michal Bieniek
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Apeiron Synthesis Sp zoo
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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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic 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
    • C07C67/30—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F132/00—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
    • C08F132/02—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
    • C08F132/06—Homopolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
    • C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
    • C08G2261/332—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3325—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing only carbon atoms derived from other polycyclic systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/418—Ring opening metathesis polymerisation [ROMP]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2875956A 2012-07-27 2013-07-26 Ruthenium complexes comprising chelating alkylidene ligands and their use as metathesis catalysts Active CA2875956C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
PL400162A PL400162A1 (pl) 2012-07-27 2012-07-27 Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
PLP.400162 2012-07-27
PCT/EP2013/065839 WO2014016422A1 (en) 2012-07-27 2013-07-26 Novel ruthenium complexes, their use in the metathesis reactions, and a process for carrying out the metathesis reaction

Publications (2)

Publication Number Publication Date
CA2875956A1 CA2875956A1 (en) 2014-01-30
CA2875956C true CA2875956C (en) 2016-01-19

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CA2875956A Active CA2875956C (en) 2012-07-27 2013-07-26 Ruthenium complexes comprising chelating alkylidene ligands and their use as metathesis catalysts

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US (1) US9328132B2 (enExample)
EP (1) EP2877478B1 (enExample)
JP (1) JP6121533B2 (enExample)
KR (1) KR101749238B1 (enExample)
CN (1) CN104428306B (enExample)
AU (1) AU2013294909B2 (enExample)
CA (1) CA2875956C (enExample)
IL (1) IL236128A (enExample)
PL (2) PL400162A1 (enExample)
RU (1) RU2586213C1 (enExample)
SG (1) SG11201408224SA (enExample)
WO (1) WO2014016422A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL400162A1 (pl) 2012-07-27 2014-02-03 Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy
PL238806B1 (pl) * 2015-09-30 2021-10-04 Apeiron Synthesis Spolka Akcyjna Kompleks rutenu i sposób jego wytwarzania, związek pośredni stosowany w tym sposobie oraz zastosowanie kompleksu rutenu i związku pośredniego w metatezie olefin
CA3006976A1 (en) * 2015-12-10 2017-06-15 California Institute Of Technology Olefin metathesis catalysts
WO2018150379A2 (en) 2017-02-17 2018-08-23 Provivi, Inc. Synthesis of pheromones and related materials via olefin metathesis
US11471867B2 (en) 2017-06-23 2022-10-18 Gwangju Institute Of Science And Technology Ligand for forming ruthenium complex, ruthenium complex catalyst, production method therefor and use thereof
TWI758525B (zh) 2017-08-10 2022-03-21 日商住友電木股份有限公司 作為光學材料之聚環烯烴聚合物組成物
TWI777027B (zh) * 2018-01-26 2022-09-11 日商住友電木股份有限公司 聚環烯烴單體及由能夠產生光酸作為光學材料的化合物活化之催化劑
TWI794520B (zh) 2018-06-29 2023-03-01 日商住友電木股份有限公司 作為 3d 列印材料之聚環烯烴單體及由能夠產生光酸之化合物活化之催化劑
US11939410B2 (en) 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
WO2020132665A1 (en) 2018-12-21 2020-06-25 Promerus, Llc High impact strength 3d printing materials derived from polycycoolefin monomers and crosslinkers
KR102670566B1 (ko) * 2019-01-18 2024-05-31 광주과학기술원 루테늄 착화합물, 이의 제조를 위한 리간드 및 이의 용도
US11692056B2 (en) 2019-07-25 2023-07-04 Promerus, Llc Stable polycycloolefin polymer and inorganic nanoparticle compositions as optical materials
CN114174373B (zh) * 2019-09-27 2024-07-30 日本瑞翁株式会社 含有聚合物的物质及其制造方法、以及膜
TWI895585B (zh) 2021-02-02 2025-09-01 日商住友電木股份有限公司 作為光學材料之保存期限長期穩定的光活性本體聚合型多環烯烴組成物
JP7792708B2 (ja) 2021-02-02 2025-12-26 アペイロン シンセシス エス アー 長い貯蔵寿命安定性のオレフィンメタセシス用の触媒（前駆体）としての有機ルテニウム錯体
JP7637829B2 (ja) 2021-11-29 2025-02-28 プロメラス， エルエルシー 光学材料として安定的な光活性塊状重合性ポリシクロオレフィン組成物を含むデュアルｕｖ遮断剤
EP4605438A1 (en) 2022-10-21 2025-08-27 Merck Patent GmbH Composition
EP4744462A1 (en) 2023-07-10 2026-05-20 Merck Patent GmbH COMPOSITION
WO2026125474A1 (en) 2024-12-12 2026-06-18 Merck Patent Gmbh Composition
WO2026125327A1 (en) 2024-12-12 2026-06-18 Merck Patent Gmbh Composition

Family Cites Families (12)

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Publication number Priority date Publication date Assignee Title
CN100509155C (zh) * 2001-03-26 2009-07-08 陶氏环球技术公司 多相催化剂组合物
AU2002307384A1 (en) * 2001-04-16 2002-10-28 California Institute Of Technology Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts
PL199412B1 (pl) * 2002-10-15 2008-09-30 Boehringer Ingelheim Int Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania
PL199428B1 (pl) 2003-12-29 2008-09-30 Polska Akademia Nauk Instytut Nowe kompleksy rutenu, pochodne 2-alkoksy-4-nitrostyrenu jako (pre)katalizatory (54) reakcji metatezy, pochodne 2-alkoksy-4-nitrostyrenu jako związki pośrednie oraz sposób ich wytwarzania
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
RU2311231C1 (ru) * 2006-08-15 2007-11-27 ООО "Объединенный центр исследований и разработок" Катализатор для получения эфиров акриловой кислоты по реакции метатезиса диалкилмалеатов (варианты) и каталитическая композиция на его основе
DE102006040569A1 (de) * 2006-08-30 2008-03-06 Lanxess Deutschland Gmbh Verfahren zum Metathese-Abbau von Nitrilkautschuken
DE102006043704A1 (de) 2006-09-18 2008-03-27 Umicore Ag & Co. Kg Neue Metathesekatalysatoren
EP2255877B1 (en) 2009-05-07 2014-09-24 Umicore AG & Co. KG Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands
RU2402572C1 (ru) * 2009-07-09 2010-10-27 Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" Способ получения полидициклопентадиена и материалов на его основе
CN102476060B (zh) * 2010-11-24 2013-07-10 中国石油化工股份有限公司 一种烯烃复分解催化剂及其制备方法
PL400162A1 (pl) 2012-07-27 2014-02-03 Apeiron Synthesis Spólka Z Ograniczona Odpowiedzialnoscia Nowe kompleksy rutenu, ich zastosowanie w reakcjach metatezy oraz sposób prowadzenia reakcji metatezy

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Publication number Publication date
AU2013294909B2 (en) 2015-11-19
EP2877478B1 (en) 2016-11-16
SG11201408224SA (en) 2015-01-29
US20150158896A1 (en) 2015-06-11
PL400162A1 (pl) 2014-02-03
JP6121533B2 (ja) 2017-04-26
CA2875956A1 (en) 2014-01-30
JP2015525776A (ja) 2015-09-07
WO2014016422A1 (en) 2014-01-30
CN104428306B (zh) 2017-05-24
US9328132B2 (en) 2016-05-03
IL236128A0 (en) 2015-02-01
KR101749238B1 (ko) 2017-06-20
PL2877478T3 (pl) 2017-05-31
IL236128A (en) 2017-07-31
AU2013294909A1 (en) 2015-01-22
EP2877478A1 (en) 2015-06-03
KR20150023672A (ko) 2015-03-05
CN104428306A (zh) 2015-03-18
RU2586213C1 (ru) 2016-06-10

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