ZA201305726B - Z-selective olefin metathesis catalysts and their synthetic procedure - Google Patents

Z-selective olefin metathesis catalysts and their synthetic procedure

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Publication number
ZA201305726B
ZA201305726B ZA2013/05726A ZA201305726A ZA201305726B ZA 201305726 B ZA201305726 B ZA 201305726B ZA 2013/05726 A ZA2013/05726 A ZA 2013/05726A ZA 201305726 A ZA201305726 A ZA 201305726A ZA 201305726 B ZA201305726 B ZA 201305726B
Authority
ZA
South Africa
Prior art keywords
synthetic procedure
olefin metathesis
metathesis catalysts
selective olefin
selective
Prior art date
Application number
ZA2013/05726A
Other languages
English (en)
Inventor
Paresma Rasiklal Patel
Bennjamin Keith Keitz
Robert Howard Grubbs
Myles Benton Herbert
Koji Endo
Original Assignee
California Inst Of Techn
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 California Inst Of Techn filed Critical California Inst Of Techn
Publication of ZA201305726B publication Critical patent/ZA201305726B/en

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2282Unsaturated compounds used as ligands
    • B01J31/2295Cyclic compounds, e.g. cyclopentadienyls
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2265Carbenes or carbynes, i.e.(image)
    • B01J31/2269Heterocyclic carbenes
    • B01J31/2273Heterocyclic carbenes with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2265Carbenes or carbynes, i.e.(image)
    • B01J31/2278Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02Metathesis reactions at an unsaturated carbon-to-carbon bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/02Metathesis reactions at an unsaturated carbon-to-carbon bond
    • C07C6/04Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/30Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333Preparation 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
    • C07C67/343Preparation 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0046Ruthenium compounds
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/54Metathesis reactions, e.g. olefin metathesis
    • B01J2231/543Metathesis reactions, e.g. olefin metathesis alkene metathesis
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261Complexes comprising ligands with non-tetrahedral chirality
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82Metals of the platinum group
    • B01J2531/821Ruthenium
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22Organic complexes
    • B01J31/2204Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208Oxygen, e.g. acetylacetonates
    • B01J31/2226Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223At least two oxygen atoms present in one at least bidentate or bridging ligand
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22Organic complexes
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/52Improvements 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)
ZA2013/05726A 2011-01-14 2013-07-29 Z-selective olefin metathesis catalysts and their synthetic procedure ZA201305726B (en)

Applications Claiming Priority (4)

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

Publications (1)

Publication Number Publication Date
ZA201305726B true ZA201305726B (en) 2018-12-19

Family

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Family Applications (2)

Application Number Title Priority Date Filing Date
ZA2013/05726A ZA201305726B (en) 2011-01-14 2013-07-29 Z-selective olefin metathesis catalysts and their synthetic procedure
ZA2014/08071A ZA201408071B (en) 2011-01-14 2014-11-04 Z-selective olefin metathesis catalysts and their synthetic procedure

Family Applications After (1)

Application Number Title Priority Date Filing Date
ZA2014/08071A ZA201408071B (en) 2011-01-14 2014-11-04 Z-selective olefin metathesis catalysts and their synthetic procedure

Country Status (13)

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

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2838359A4 (en) 2012-03-05 2015-12-09 California Inst Of Techn SYNTHESIS OF Z-OLEFIN-CONTAINING PHEROMONES OF LEPIDOPTERA INSECTS
JP6092379B2 (ja) 2012-06-29 2017-03-08 アペイロン シンセシス エス アー 金属錯体、その適用、及びメタセシス反応の実施方法
US9147844B2 (en) 2012-08-01 2015-09-29 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
BR112015013580A2 (pt) 2012-12-12 2017-07-11 California Inst Of Techn catalisador de metátese z-seletiva
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
ES2699416T3 (es) 2013-04-09 2019-02-11 Materia Inc Preparación de tensioactivos mediante metátesis cruzada
US20160101414A1 (en) * 2013-05-15 2016-04-14 California Institute Of Technology Highly z-selective and enantioselective ring opening/cross metathesis catalyzed by a resolved stereogenic-at-ru complex
EP3008078B1 (en) 2013-06-12 2018-12-19 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
PL3353187T3 (pl) * 2015-09-24 2021-11-22 Umicore Ag & Co. Kg Katalizatory metatezy olefin na bazie karbenu metalu
KR20180116238A (ko) 2015-12-10 2018-10-24 우미코레 아게 운트 코 카게 올레핀 복분해 촉매
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
WO2018220088A1 (en) 2017-05-30 2018-12-06 Ximo Ag Methods of making olefinic e- and z-isomers
EP3762143A1 (en) * 2018-03-09 2021-01-13 PPG Industries Ohio Inc. Compounds for coordinating with a metal, compositions containing such compounds, and methods of catalyzing reactions
CN112119055A (zh) * 2018-05-15 2020-12-22 加利福尼亚技术学院 通过立体保留性复分解全合成前列腺素j天然产物
US11939410B2 (en) * 2018-06-29 2024-03-26 Apeiron Synthesis S.A. Organoruthenium complexes as precatalysts for olefin metathesis
CN114206889A (zh) * 2019-07-17 2022-03-18 加利福尼亚技术学院 Z选择性烯烃复分解催化剂的新合成
EP4069667A1 (en) * 2020-03-05 2022-10-12 Firmenich SA Process for preparing perfuming intermediate
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
CN118056617A (zh) * 2022-11-15 2024-05-21 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

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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
JP3943015B2 (ja) 2000-08-10 2007-07-11 トラスティーズ オブ ボストン カレッジ リサイクル可能メタセシス触媒
US6620955B1 (en) 2001-11-15 2003-09-16 Richard L. Pederson 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
AU2005252276B2 (en) * 2004-06-09 2010-10-14 Uti Limited Partnership Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions
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
WO2007003135A1 (en) * 2005-07-04 2007-01-11 Zheng-Yun Zhan Ruthenium complex ligand, ruthenium complex, carried ruthenium complex catalyst and the preparing methods and the use thereof
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

Also Published As

Publication number Publication date
US20140106960A1 (en) 2014-04-17
IL227432A0 (en) 2013-09-30
JP2014503356A (ja) 2014-02-13
EP2663398A4 (en) 2014-07-23
CA2824518A1 (en) 2012-07-19
BR112013017938A2 (pt) 2018-11-27
BR112013017938B1 (pt) 2019-10-15
ZA201408071B (en) 2019-06-26
EP2663398B1 (en) 2018-07-18
US9597674B2 (en) 2017-03-21
WO2012097379A2 (en) 2012-07-19
KR101835170B1 (ko) 2018-03-06
JP5893646B2 (ja) 2016-03-23
WO2012097379A3 (en) 2012-10-11
CA2824518C (en) 2019-03-26
PL2663398T3 (pl) 2019-01-31
AU2012206966B2 (en) 2016-11-17
KR20140021995A (ko) 2014-02-21
IL227432A (en) 2017-12-31
CN103402628A (zh) 2013-11-20
SG191980A1 (en) 2013-08-30
CN103402628B (zh) 2015-12-23
EP2663398A2 (en) 2013-11-20

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