PL441535A1 - Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin - Google Patents

Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin

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Publication number
PL441535A1
PL441535A1 PL441535A PL44153522A PL441535A1 PL 441535 A1 PL441535 A1 PL 441535A1 PL 441535 A PL441535 A PL 441535A PL 44153522 A PL44153522 A PL 44153522A PL 441535 A1 PL441535 A1 PL 441535A1
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PL
Poland
Prior art keywords
ruthenium complexes
new ruthenium
obtaining
preparation
olefin metathesis
Prior art date
Application number
PL441535A
Other languages
English (en)
Inventor
Karol Grela
Anna KAJETANOWICZ
Adrian SYTNICZUK
Mariusz MILEWSKI
Vishal Purohit
Filip STRUZIK
Original Assignee
Uniwersytet Warszawski
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.)
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Publication date
Application filed by Uniwersytet Warszawski filed Critical Uniwersytet Warszawski
Priority to PL441535A priority Critical patent/PL441535A1/pl
Priority to KR1020257001837A priority patent/KR20250040634A/ko
Priority to PCT/IB2023/056530 priority patent/WO2023248205A1/en
Priority to JP2024575547A priority patent/JP2025522560A/ja
Priority to EP23768935.1A priority patent/EP4543894A1/en
Publication of PL441535A1 publication Critical patent/PL441535A1/pl

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • 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)
    • 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
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • 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
    • C07C67/00—Preparation of carboxylic acid esters
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, 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 or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • B01J2531/0286—Complexes comprising ligands or other components characterized by their function
    • B01J2531/0288—Sterically demanding or shielding ligands
    • 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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Przedmiotem zgłoszenia jest nowy kompleks rutenu, w którym wszystkie zmienne mają zdefiniowane w opisie znaczenia. Przedmiotem zgłoszenia jest także sposób otrzymywania kompleksu rutenu, związek pośredni będący prekursorem ligandu stosowany w otrzymywania kompleksu rutenu CAAC-1 oraz zastosowanie tego kompleksu rutenu jako (pre)katalizatora w reakcjach metatezy olefin.
PL441535A 2022-06-23 2022-06-23 Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin PL441535A1 (pl)

Priority Applications (5)

Application Number Priority Date Filing Date Title
PL441535A PL441535A1 (pl) 2022-06-23 2022-06-23 Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin
KR1020257001837A KR20250040634A (ko) 2022-06-23 2023-06-23 신규한 루테늄 복합체, 이의 합성 방법, 이러한 방법에서 사용되는 중간체 화합물, 이의 합성 방법 및 올레핀 복분해 반응에서의 신규한 루테늄 복합체의 용도
PCT/IB2023/056530 WO2023248205A1 (en) 2022-06-23 2023-06-23 Novel ruthenium complexes, method of their synthesis, intermediate compounds used in this method, method of their synthesis and the use of novel ruthenium complexes in olefin metathesis reactions
JP2024575547A JP2025522560A (ja) 2022-06-23 2023-06-23 新規ルテニウム錯体、その合成の方法、この方法に使用される中間化合物、その合成の方法、及びオレフィンメタセシス反応における新規ルテニウム錯体の使用
EP23768935.1A EP4543894A1 (en) 2022-06-23 2023-06-23 Novel ruthenium complexes, method of their synthesis, intermediate compounds used in this method, method of their synthesis and the use of novel ruthenium complexes in olefin metathesis reactions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PL441535A PL441535A1 (pl) 2022-06-23 2022-06-23 Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin

Publications (1)

Publication Number Publication Date
PL441535A1 true PL441535A1 (pl) 2023-12-27

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PL441535A PL441535A1 (pl) 2022-06-23 2022-06-23 Nowe kompleksy rutenu, sposób ich otrzymywania, związki pośrednie stosowane w tym sposobie, sposób ich wytwarzania oraz zastosowanie nowych kompleksów rutenu w reakcjach metatezy olefin

Country Status (5)

Country Link
EP (1) EP4543894A1 (pl)
JP (1) JP2025522560A (pl)
KR (1) KR20250040634A (pl)
PL (1) PL441535A1 (pl)
WO (1) WO2023248205A1 (pl)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9249170B2 (en) * 2013-04-11 2016-02-02 California Institute Of Technology Cyclic alkyl amino carbene (CAAC) ruthenium complexes as improved catalysts for ethenolysis reactions
PL414234A1 (pl) * 2015-09-30 2017-04-10 Apeiron Synthesis Spółka Akcyjna Sposób wytwarzania kompleksów rutenu i związków pośrednich oraz ich zastosowanie w metatezie olefin
WO2018087678A1 (en) * 2016-11-10 2018-05-17 Apeiron Synthesis S.A. Use of ruthenium complexes in olefin metathesis reaction
WO2022008656A1 (en) * 2020-07-08 2022-01-13 Centre National De La Recherche Scientifique Optically pure enantiomers of ruthenium complexes and uses thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3129347T3 (pl) * 2014-04-10 2022-02-07 California Institute Of Technology Reakcje w obecności kompleksów rutenu

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9249170B2 (en) * 2013-04-11 2016-02-02 California Institute Of Technology Cyclic alkyl amino carbene (CAAC) ruthenium complexes as improved catalysts for ethenolysis reactions
PL414234A1 (pl) * 2015-09-30 2017-04-10 Apeiron Synthesis Spółka Akcyjna Sposób wytwarzania kompleksów rutenu i związków pośrednich oraz ich zastosowanie w metatezie olefin
WO2018087678A1 (en) * 2016-11-10 2018-05-17 Apeiron Synthesis S.A. Use of ruthenium complexes in olefin metathesis reaction
WO2022008656A1 (en) * 2020-07-08 2022-01-13 Centre National De La Recherche Scientifique Optically pure enantiomers of ruthenium complexes and uses thereof

Also Published As

Publication number Publication date
JP2025522560A (ja) 2025-07-15
EP4543894A1 (en) 2025-04-30
KR20250040634A (ko) 2025-03-24
WO2023248205A1 (en) 2023-12-28

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