JP2004506644A - カルベノイド含有ルテニウム錯体 - Google Patents
カルベノイド含有ルテニウム錯体 Download PDFInfo
- Publication number
- JP2004506644A JP2004506644A JP2002519473A JP2002519473A JP2004506644A JP 2004506644 A JP2004506644 A JP 2004506644A JP 2002519473 A JP2002519473 A JP 2002519473A JP 2002519473 A JP2002519473 A JP 2002519473A JP 2004506644 A JP2004506644 A JP 2004506644A
- Authority
- JP
- Japan
- Prior art keywords
- independently
- ruthenium complex
- rucl
- ligand
- group
- 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.)
- Withdrawn
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- 239000012327 Ruthenium complex Substances 0.000 title claims description 16
- 239000003446 ligand Substances 0.000 claims abstract description 41
- 230000007935 neutral effect Effects 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 5
- 125000000129 anionic group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 150000003303 ruthenium Chemical class 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 34
- -1 acyclic diaminocarbenes Chemical class 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000005865 alkene metathesis reaction Methods 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229940052810 complex b Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000013522 chelant Substances 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 15
- 238000005649 metathesis reaction Methods 0.000 description 11
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 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 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 238000010535 acyclic diene metathesis reaction Methods 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
- 101150065749 Churc1 gene Proteins 0.000 description 2
- 102100038239 Protein Churchill Human genes 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005686 cross metathesis reaction Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000005872 self-metathesis reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 108010085082 sigma receptors Proteins 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10039389A DE10039389A1 (de) | 2000-08-11 | 2000-08-11 | Carbenoide enthaltende Rutheniumkomplexe |
| PCT/EP2001/009295 WO2002014336A1 (de) | 2000-08-11 | 2001-08-10 | Carbenoide enthaltende rutheniumkomplexe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506644A true JP2004506644A (ja) | 2004-03-04 |
| JP2004506644A5 JP2004506644A5 (cg-RX-API-DMAC7.html) | 2005-03-03 |
Family
ID=7652191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002519473A Withdrawn JP2004506644A (ja) | 2000-08-11 | 2001-08-10 | カルベノイド含有ルテニウム錯体 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20030195357A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1311520A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2004506644A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20030022888A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1447815A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2001287677A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2419368A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE10039389A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA200300260A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA03001161A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002014336A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI295410B (en) * | 2002-11-29 | 2008-04-01 | Zeon Corp | Radiation-sensitive resin composition |
| US7094898B2 (en) * | 2003-05-29 | 2006-08-22 | University Of Ottawa | Ruthenium compounds, their production and use |
| CN100569662C (zh) * | 2007-12-12 | 2009-12-16 | 中国科学院长春应用化学研究所 | 有机配体包覆的氧化钌纳米粒子的制备方法 |
| US8759541B2 (en) * | 2008-07-08 | 2014-06-24 | Avinash N. Thadani | Chiral acyclic diaminocarbene ligands, precursors therefore and their use in organic synthesis reactions |
| GB0822064D0 (en) * | 2008-12-03 | 2009-01-07 | Johnson Matthey Plc | Process for preparing cationic ruthenium complexes |
| WO2011059803A2 (en) * | 2009-10-29 | 2011-05-19 | Board Of Regents, The University Of Texas System | Ruthenium-alkylidenes containing acyclic diaminocarbenes for obtaining low e/z ratios in cross metathesis |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5160926A (en) * | 1989-06-28 | 1992-11-03 | Schweitzer Engineering Laboratories, Inc. | Display transducer apparatus |
| US6011480A (en) * | 1997-07-23 | 2000-01-04 | Schweitzer Engineering Laboratories, Inc. | Protection quality capability for protective relays used in an electric power system |
| DE19902439A1 (de) * | 1999-01-22 | 2000-08-03 | Aventis Res & Tech Gmbh & Co | Homo- und heterobimetallische Alkylidenkomplexe des Rutheniums mit N-heterocyclischen Carbenliganden und deren Anwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
-
2000
- 2000-08-11 DE DE10039389A patent/DE10039389A1/de not_active Withdrawn
-
2001
- 2001-08-10 US US10/344,367 patent/US20030195357A1/en not_active Abandoned
- 2001-08-10 JP JP2002519473A patent/JP2004506644A/ja not_active Withdrawn
- 2001-08-10 CA CA002419368A patent/CA2419368A1/en not_active Abandoned
- 2001-08-10 CN CN01814516A patent/CN1447815A/zh active Pending
- 2001-08-10 KR KR10-2003-7001939A patent/KR20030022888A/ko not_active Withdrawn
- 2001-08-10 WO PCT/EP2001/009295 patent/WO2002014336A1/de not_active Ceased
- 2001-08-10 EA EA200300260A patent/EA200300260A1/ru unknown
- 2001-08-10 AU AU2001287677A patent/AU2001287677A1/en not_active Abandoned
- 2001-08-10 EP EP01967261A patent/EP1311520A1/de not_active Withdrawn
- 2001-08-10 MX MXPA03001161A patent/MXPA03001161A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001287677A1 (en) | 2002-02-25 |
| DE10039389A1 (de) | 2002-02-21 |
| CN1447815A (zh) | 2003-10-08 |
| EP1311520A1 (de) | 2003-05-21 |
| WO2002014336A1 (de) | 2002-02-21 |
| CA2419368A1 (en) | 2003-02-10 |
| EA200300260A1 (ru) | 2003-08-28 |
| MXPA03001161A (es) | 2003-10-14 |
| US20030195357A1 (en) | 2003-10-16 |
| KR20030022888A (ko) | 2003-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20081104 |