JP2009519947A5 - - Google Patents
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- Publication number
- JP2009519947A5 JP2009519947A5 JP2008545845A JP2008545845A JP2009519947A5 JP 2009519947 A5 JP2009519947 A5 JP 2009519947A5 JP 2008545845 A JP2008545845 A JP 2008545845A JP 2008545845 A JP2008545845 A JP 2008545845A JP 2009519947 A5 JP2009519947 A5 JP 2009519947A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- group
- nhc
- carbene
- 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.)
- Granted
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- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 claims 31
- 239000003054 catalyst Substances 0.000 claims 16
- -1 nitroso, sulfo, sulfonato, boryl Chemical group 0.000 claims 15
- 229910052707 ruthenium Inorganic materials 0.000 claims 15
- 239000003446 ligand Substances 0.000 claims 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 238000005865 alkene metathesis reaction Methods 0.000 claims 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 150000001336 alkenes Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 238000005649 metathesis reaction Methods 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 4
- 150000004820 halides Chemical class 0.000 claims 4
- 125000000743 hydrocarbylene group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 3
- 239000013522 chelant Substances 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 229910052698 phosphorus Inorganic materials 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- QFAKXSUNHTXHAE-UHFFFAOYSA-N OS(=O)(=O)S(=O)(=O)ON=O Chemical compound OS(=O)(=O)S(=O)(=O)ON=O QFAKXSUNHTXHAE-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000000707 boryl group Chemical group B* 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- CLMJEWSUQLNMEF-UHFFFAOYSA-N B(O)(O)OP(=O)(O)P(=O)(O)O Chemical compound B(O)(O)OP(=O)(O)P(=O)(O)O CLMJEWSUQLNMEF-UHFFFAOYSA-N 0.000 claims 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000000746 allylic group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 229910000074 antimony hydride Inorganic materials 0.000 claims 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000005686 cross metathesis reaction Methods 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000002390 heteroarenes Chemical class 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 125000005538 phosphinite group Chemical group 0.000 claims 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- QRTHECVGSAZOPL-UHFFFAOYSA-N thiocyanato cyanate Chemical compound N#COSC#N QRTHECVGSAZOPL-UHFFFAOYSA-N 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 0 CC(N(CC1)CN1c1cc(*)c(*)c(*)c1*)=C(*)C(*)=C(*)C(*)=C Chemical compound CC(N(CC1)CN1c1cc(*)c(*)c(*)c1*)=C(*)C(*)=C(*)C(*)=C 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75122505P | 2005-12-16 | 2005-12-16 | |
| US60/751,225 | 2005-12-16 | ||
| US80174206P | 2006-05-19 | 2006-05-19 | |
| US60/801,742 | 2006-05-19 | ||
| US85371706P | 2006-10-19 | 2006-10-19 | |
| US60/853,717 | 2006-10-19 | ||
| US85914806P | 2006-11-15 | 2006-11-15 | |
| US60/859,148 | 2006-11-15 | ||
| PCT/US2006/047934 WO2007075427A1 (en) | 2005-12-16 | 2006-12-18 | Organometallic ruthenium complexes and related methods for the preparation of tetra-substituted and other hindered olefins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009519947A JP2009519947A (ja) | 2009-05-21 |
| JP2009519947A5 true JP2009519947A5 (OSRAM) | 2010-02-18 |
| JP5522941B2 JP5522941B2 (ja) | 2014-06-18 |
Family
ID=37964546
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008545845A Expired - Fee Related JP5522941B2 (ja) | 2005-12-16 | 2006-12-18 | 有機金属ルテニウム錯体および関連する四置換および別の嵩高いオレフィンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8008224B2 (OSRAM) |
| EP (1) | EP1971616A1 (OSRAM) |
| JP (1) | JP5522941B2 (OSRAM) |
| KR (2) | KR20080103961A (OSRAM) |
| CN (1) | CN101460513B (OSRAM) |
| SG (1) | SG169326A1 (OSRAM) |
| WO (1) | WO2007075427A1 (OSRAM) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8877936B2 (en) * | 2008-04-09 | 2014-11-04 | California Institute Of Technology | Ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene ligands with substituted backbone |
| FR2939331B1 (fr) | 2008-12-10 | 2012-08-10 | Inst Francais Du Petrole | Composition catalytique et procede de metathese de corps gras insature |
| EA020900B1 (ru) | 2009-05-05 | 2015-02-27 | Стипэн Компани | Композиция для добычи нефти, способ добычи нефти из нефтеносного пласта и сульфонированное производное внутренних олефинов |
| WO2011135029A1 (en) | 2010-04-28 | 2011-11-03 | Dsm Ip Assets B.V. | Metathesis crosslinkable coating compositions |
| JP5674059B2 (ja) * | 2011-01-24 | 2015-02-25 | 国立大学法人名古屋大学 | ルテニウム錯体を含む水素移動反応用触媒及び水素移動反応物の製造方法 |
| CN102145304B (zh) * | 2011-02-24 | 2012-08-08 | 华东师范大学 | 一种负载型格拉布斯催化剂的制备及其应用 |
| FR2983475B1 (fr) | 2011-12-02 | 2014-01-17 | IFP Energies Nouvelles | Procede de metathese d'olefines lineaires alpha utilisant un complexe du ruthenium comportant un carbene n-heterocyclique dissymetrique |
| KR20150034679A (ko) | 2012-06-29 | 2015-04-03 | 아페이론 신세시스 에스.아. | 금속 착체, 이의 용도 및 복분해 반응의 실시 방법 |
| PL225024B1 (pl) | 2012-08-16 | 2017-02-28 | Univ Warszawski | Nowe kompleksy rutenu oraz ich zastosowanie |
| US10500577B2 (en) | 2015-07-20 | 2019-12-10 | CE Pharm CO., LTD | Oxalic amide ligands, and uses thereof in copper-catalyzed coupling reaction of aryl halides |
| EP4234522A3 (en) | 2015-11-18 | 2023-10-25 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
| HUE053613T2 (hu) | 2015-11-18 | 2021-07-28 | Provivi Inc | Mikroorganizmusok rovarferomonok és kapcsolódó vegyületek elõállítására |
| PL3386936T3 (pl) * | 2015-12-10 | 2024-10-07 | Umicore Ag & Co. Kg | Katalizatory metatezy olefin |
| EP3464311A4 (en) | 2016-06-06 | 2020-03-18 | Provivi, Inc. | SEMI-BIOSYNTHETIC PRODUCTION OF FATTY ALCOHOLS AND FATTY ALDEHYDES |
| WO2018150379A2 (en) | 2017-02-17 | 2018-08-23 | Provivi, Inc. | Synthesis of pheromones and related materials via olefin metathesis |
| JP7216018B2 (ja) | 2017-05-17 | 2023-01-31 | プロヴィヴィ インコーポレイテッド | 昆虫フェロモンの生成のための微生物及び関連する化合物 |
| US10683388B2 (en) * | 2017-08-15 | 2020-06-16 | University Of Florida Research Foundation, Incorporated | High temperature metathesis chemistry |
| CN108299506A (zh) * | 2018-01-29 | 2018-07-20 | 中国科学院成都有机化学有限公司 | N-杂环卡宾钌络合物及其制备方法和用途 |
| CN109225334B (zh) * | 2018-07-20 | 2021-05-18 | 吉林化工学院 | 一种具有邻位空间位阻结构的钌烯烃复分解催化剂及其制备方法和应用 |
| CN109364998B (zh) * | 2018-10-15 | 2021-07-06 | 天津科技大学 | 一种用于烯烃复分解反应的催化剂及其制备和应用方法 |
| CN111250168B (zh) * | 2018-11-30 | 2021-06-01 | 中国科学院大连化学物理研究所 | 一种钌基催化剂及其制备方法、应用 |
| CN110041262B (zh) * | 2019-01-02 | 2020-03-27 | 成都开美思商务信息咨询中心(有限合伙) | 氮杂环卡宾配体及其钌催化剂、制备方法和应用 |
| CN112547126B (zh) * | 2020-12-21 | 2023-03-21 | 上海中化科技有限公司 | 钌卡宾化合物、其组合物、制备方法及应用 |
| CN113000066B (zh) * | 2021-01-09 | 2022-04-12 | 河南大学 | 一种z-选择性钌卡宾烯烃复分解催化剂及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| ATE248182T1 (de) * | 1999-05-24 | 2003-09-15 | California Inst Of Techn | Imidazolidin enthaltende metallcarben- katalysatoren für die metathese |
| AU2001284773B2 (en) * | 2000-08-10 | 2004-08-05 | Trustees Of Boston College | Recyclable metathesis catalysts |
| US6610626B2 (en) * | 2000-09-05 | 2003-08-26 | Cymetech, Llp | Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors |
| US6759537B2 (en) * | 2001-03-23 | 2004-07-06 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| CA2442368C (en) * | 2001-03-30 | 2015-10-13 | California Institute Of Technology | Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts |
| EP1395616B1 (en) | 2001-04-16 | 2019-05-22 | California Institute Of Technology | Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts |
| US6818586B2 (en) * | 2001-08-01 | 2004-11-16 | Cymetech, Llp | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| EP2251360B1 (en) * | 2001-08-29 | 2013-07-31 | California Institute of Technology | Ring-opening metathesis polymerization of bridged bicyclic and polycyclic olefins containing two or more heteroatoms |
-
2006
- 2006-12-18 KR KR1020087017250A patent/KR20080103961A/ko not_active Ceased
- 2006-12-18 EP EP06845551A patent/EP1971616A1/en not_active Withdrawn
- 2006-12-18 US US11/640,400 patent/US8008224B2/en active Active
- 2006-12-18 SG SG201100293-8A patent/SG169326A1/en unknown
- 2006-12-18 JP JP2008545845A patent/JP5522941B2/ja not_active Expired - Fee Related
- 2006-12-18 WO PCT/US2006/047934 patent/WO2007075427A1/en not_active Ceased
- 2006-12-18 KR KR1020147019358A patent/KR20140097571A/ko not_active Ceased
- 2006-12-18 CN CN200680051426.3A patent/CN101460513B/zh not_active Expired - Fee Related
-
2011
- 2011-08-30 US US13/221,871 patent/US8361922B2/en active Active
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