JP5893646B2 - Ｚ選択的オレフィンメタセシス触媒及びその合成手順 - Google Patents
Ｚ選択的オレフィンメタセシス触媒及びその合成手順 Download PDFInfo
- Publication number
- JP5893646B2 JP5893646B2 JP2013549616A JP2013549616A JP5893646B2 JP 5893646 B2 JP5893646 B2 JP 5893646B2 JP 2013549616 A JP2013549616 A JP 2013549616A JP 2013549616 A JP2013549616 A JP 2013549616A JP 5893646 B2 JP5893646 B2 JP 5893646B2
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- heteroatom
- aryl
- hydrocarbyl
- alkyl
- 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.)
- Expired - Fee Related
Links
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
-
- 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
- B01J31/02—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
Landscapes
- 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2014503356A JP2014503356A (ja) | 2014-02-13 |
| JP2014503356A5 JP2014503356A5 (enExample) | 2015-02-26 |
| JP5893646B2 true JP5893646B2 (ja) | 2016-03-23 |
Family
ID=46507707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013549616A Expired - Fee Related JP5893646B2 (ja) | 2011-01-14 | 2012-01-17 | Ｚ選択的オレフィンメタセシス触媒及びその合成手順 |
Country Status (13)
| Country | Link |
|---|---|
| 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 (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8987531B2 (en) | 2012-03-05 | 2015-03-24 | California Institute Of Technology | Syntheses of Z-olefin-containing lepidopteran insect pheromones |
| CN104350060B (zh) | 2012-06-29 | 2017-09-12 | 阿派朗合成公司 | 金属络合物、其应用和进行复分解反应的方法 |
| 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 |
| US9586981B2 (en) | 2012-12-12 | 2017-03-07 | California Institute Of Technology | Z-selective metathesis catalysts |
| US9758445B2 (en) | 2013-04-09 | 2017-09-12 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| BR112015025850B1 (pt) | 2013-04-09 | 2021-11-03 | Materia, Inc | Método para produzir pelo menos um produto de metátese cruzada |
| EP2984055B1 (en) * | 2013-04-09 | 2018-10-17 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| WO2014186631A1 (en) * | 2013-05-15 | 2014-11-20 | California Institute Of Technology | Highly z-selective and enantioselective ring opening/cross metathesis |
| 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 |
| MX2018003639A (es) * | 2015-09-24 | 2019-04-25 | Umicore Ag & Co Kg | Catalizadores metálicos de metátesis olefínica de carbeno. |
| WO2017100585A1 (en) | 2015-12-10 | 2017-06-15 | Materia, Inc. | Olefin metathesis catalysts |
| US10792651B2 (en) * | 2016-10-19 | 2020-10-06 | Umicore Ag & Co. Kg | Synthesis and characterization of Ru alkylidene complexes |
| 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 |
| KR20200130398A (ko) * | 2018-03-09 | 2020-11-18 | 피피지 인더스트리즈 오하이오 인코포레이티드 | 금속과 배위하는 화합물, 그러한 화합물을 함유하는 조성물, 및 반응을 촉매하는 방법 |
| 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 |
| EP3814363B1 (en) * | 2018-06-29 | 2023-12-27 | 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 |
| WO2021183669A1 (en) * | 2020-03-13 | 2021-09-16 | The Board Of Trustees Of The University Of Illinois | Methods for catalytic hydrosilylation |
| 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 |
Family Cites Families (10)
| 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 |
| CA2419485C (en) | 2000-08-10 | 2007-10-30 | The Trustees Of Boston College | Recyclable metathesis catalysts |
| WO2003044060A2 (en) | 2001-11-15 | 2003-05-30 | Materia, Inc. | Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts |
| US7598330B2 (en) * | 2002-04-05 | 2009-10-06 | California Institute Of Technology | Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts |
| US7365140B2 (en) | 2004-06-09 | 2008-04-29 | 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 |
| EP2886549A1 (en) * | 2005-07-04 | 2015-06-24 | Zannan Scitech Co., Ltd. | Ruthenium complex ligand, ruthenium complex and the use of the complex as a catalyst in olefin metathesis reactions |
| CN102083798B (zh) * | 2008-04-09 | 2016-10-26 | 马特里亚公司 | 带有具有取代骨架的n-杂环卡宾配体的钌烯烃易位催化剂 |
| EP2255877B1 (en) | 2009-05-07 | 2014-09-24 | Umicore AG & Co. KG | Method for preparation of ruthenium-based metathesis catalysts with chelating alkylidene ligands |
-
2012
- 2012-01-17 JP JP2013549616A patent/JP5893646B2/ja not_active Expired - Fee Related
- 2012-01-17 US US13/978,940 patent/US9597674B2/en active Active
- 2012-01-17 BR BR112013017938-4A patent/BR112013017938B1/pt active IP Right Grant
- 2012-01-17 SG SG2013054085A patent/SG191980A1/en unknown
- 2012-01-17 WO PCT/US2012/021609 patent/WO2012097379A2/en not_active Ceased
- 2012-01-17 EP EP12734668.2A patent/EP2663398B1/en active Active
- 2012-01-17 CN CN201280010878.2A patent/CN103402628B/zh active Active
- 2012-01-17 KR KR1020137021063A patent/KR101835170B1/ko not_active Expired - Fee Related
- 2012-01-17 AU AU2012206966A patent/AU2012206966B2/en not_active Ceased
- 2012-01-17 CA CA2824518A patent/CA2824518C/en not_active Expired - Fee Related
- 2012-01-17 PL PL12734668T patent/PL2663398T3/pl unknown
-
2013
- 2013-07-11 IL IL227432A patent/IL227432A/en active IP Right Grant
- 2013-07-29 ZA ZA2013/05726A patent/ZA201305726B/en unknown
-
2014
- 2014-11-04 ZA ZA2014/08071A patent/ZA201408071B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2663398T3 (pl) | 2019-01-31 |
| CA2824518C (en) | 2019-03-26 |
| KR101835170B1 (ko) | 2018-03-06 |
| KR20140021995A (ko) | 2014-02-21 |
| US9597674B2 (en) | 2017-03-21 |
| CN103402628B (zh) | 2015-12-23 |
| EP2663398B1 (en) | 2018-07-18 |
| WO2012097379A2 (en) | 2012-07-19 |
| CA2824518A1 (en) | 2012-07-19 |
| BR112013017938A2 (pt) | 2018-11-27 |
| AU2012206966B2 (en) | 2016-11-17 |
| EP2663398A2 (en) | 2013-11-20 |
| ZA201408071B (en) | 2019-06-26 |
| JP2014503356A (ja) | 2014-02-13 |
| BR112013017938B1 (pt) | 2019-10-15 |
| SG191980A1 (en) | 2013-08-30 |
| IL227432A (en) | 2017-12-31 |
| IL227432A0 (en) | 2013-09-30 |
| ZA201305726B (en) | 2018-12-19 |
| US20140106960A1 (en) | 2014-04-17 |
| CN103402628A (zh) | 2013-11-20 |
| EP2663398A4 (en) | 2014-07-23 |
| WO2012097379A3 (en) | 2012-10-11 |
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