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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP2663398B1 (OSRAM) |
| JP (1) | JP5893646B2 (OSRAM) |
| KR (1) | KR101835170B1 (OSRAM) |
| CN (1) | CN103402628B (OSRAM) |
| AU (1) | AU2012206966B2 (OSRAM) |
| BR (1) | BR112013017938B1 (OSRAM) |
| CA (1) | CA2824518C (OSRAM) |
| IL (1) | IL227432A (OSRAM) |
| PL (1) | PL2663398T3 (OSRAM) |
| SG (1) | SG191980A1 (OSRAM) |
| WO (1) | WO2012097379A2 (OSRAM) |
| ZA (2) | ZA201305726B (OSRAM) |
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 |
| KR20150034679A (ko) | 2012-06-29 | 2015-04-03 | 아페이론 신세시스 에스.아. | 금속 착체, 이의 용도 및 복분해 반응의 실시 방법 |
| 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 |
| CN104854119B (zh) | 2012-12-12 | 2017-09-08 | 加州理工学院 | Z‑选择性复分解催化剂 |
| WO2014169055A1 (en) * | 2013-04-09 | 2014-10-16 | 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 |
| US9758445B2 (en) | 2013-04-09 | 2017-09-12 | Materia, Inc. | Preparation of surfactants via cross-metathesis |
| 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 |
| WO2014201300A1 (en) | 2013-06-12 | 2014-12-18 | 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 |
| BR112018005823A2 (pt) * | 2015-09-24 | 2018-10-16 | Umicore Ag & Co Kg | catalisadores de metátese de metal-carbeno-olefina |
| PL3386936T3 (pl) | 2015-12-10 | 2024-10-07 | Umicore Ag & Co. Kg | Katalizatory metatezy olefin |
| 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 |
| US11618756B2 (en) * | 2018-03-09 | 2023-04-04 | Ppg Industries Ohio, Inc. | Compounds for coordinating with a metal, compositions containing such compounds, and methods of catalyzing reactions |
| JP7368381B2 (ja) | 2018-05-15 | 2023-10-24 | カリフォルニア・インスティテュート・オブ・テクノロジー | 立体保持メタセシスによるプロスタグランジンｊ天然物の全合成 |
| JP7466908B2 (ja) * | 2018-06-29 | 2024-04-15 | アペイロン シンセシス エス アー | 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 |
| JP2022542784A (ja) * | 2019-07-17 | 2022-10-07 | カリフォルニア・インスティテュート・オブ・テクノロジー | Ｚ選択的オレフィンメタセシス触媒の新合成 |
| EP4069667A1 (en) * | 2020-03-05 | 2022-10-12 | Firmenich SA | Process for preparing perfuming intermediate |
| JP2023518157A (ja) * | 2020-03-13 | 2023-04-28 | ザ ボード オブ トラスティーズ オブ ザ ユニヴァーシティー オブ イリノイ | 触媒的ヒドロシリル化のための方法 |
| 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 |
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 |
| AU2001284773B2 (en) | 2000-08-10 | 2004-08-05 | Trustees Of Boston College | Recyclable metathesis catalysts |
| 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 |
| 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 |
| RU2435778C2 (ru) | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения |
| 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 |
-
2012
- 2012-01-17 AU AU2012206966A patent/AU2012206966B2/en not_active Ceased
- 2012-01-17 PL PL12734668T patent/PL2663398T3/pl unknown
- 2012-01-17 SG SG2013054085A patent/SG191980A1/en unknown
- 2012-01-17 JP JP2013549616A patent/JP5893646B2/ja not_active Expired - Fee Related
- 2012-01-17 BR BR112013017938-4A patent/BR112013017938B1/pt active IP Right Grant
- 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 CA CA2824518A patent/CA2824518C/en not_active Expired - Fee Related
- 2012-01-17 KR KR1020137021063A patent/KR101835170B1/ko not_active Expired - Fee Related
- 2012-01-17 US US13/978,940 patent/US9597674B2/en active Active
-
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 |
|---|---|
| WO2012097379A3 (en) | 2012-10-11 |
| EP2663398B1 (en) | 2018-07-18 |
| BR112013017938A2 (pt) | 2018-11-27 |
| EP2663398A2 (en) | 2013-11-20 |
| CN103402628A (zh) | 2013-11-20 |
| KR101835170B1 (ko) | 2018-03-06 |
| CN103402628B (zh) | 2015-12-23 |
| CA2824518C (en) | 2019-03-26 |
| SG191980A1 (en) | 2013-08-30 |
| WO2012097379A2 (en) | 2012-07-19 |
| CA2824518A1 (en) | 2012-07-19 |
| ZA201305726B (en) | 2018-12-19 |
| BR112013017938B1 (pt) | 2019-10-15 |
| PL2663398T3 (pl) | 2019-01-31 |
| US20140106960A1 (en) | 2014-04-17 |
| JP2014503356A (ja) | 2014-02-13 |
| KR20140021995A (ko) | 2014-02-21 |
| IL227432A0 (en) | 2013-09-30 |
| ZA201408071B (en) | 2019-06-26 |
| US9597674B2 (en) | 2017-03-21 |
| IL227432A (en) | 2017-12-31 |
| EP2663398A4 (en) | 2014-07-23 |
| AU2012206966B2 (en) | 2016-11-17 |
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Legal Events
| Date | Code | Title | Description |
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