ME00345B - Rutenijumski kompleksi kao (pred)-katalizatori metateznih reakcija - Google Patents
Rutenijumski kompleksi kao (pred)-katalizatori metateznih reakcijaInfo
- Publication number
- ME00345B ME00345B MEP-2008-515A MEP51508A ME00345B ME 00345 B ME00345 B ME 00345B ME P51508 A MEP51508 A ME P51508A ME 00345 B ME00345 B ME 00345B
- Authority
- ME
- Montenegro
- Prior art keywords
- alkyl
- group
- formula
- compound
- aryl
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims 3
- 238000005649 metathesis reaction Methods 0.000 title claims 2
- 150000003303 ruthenium Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000003446 ligand Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 6
- 239000012327 Ruthenium complex Substances 0.000 claims 3
- -1 2,6-dimethylphenyl Chemical group 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 238000006772 olefination reaction Methods 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000005282 allenyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 238000005686 cross metathesis reaction Methods 0.000 claims 1
- 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 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Indole Compounds (AREA)
Claims (19)
1. Jedinjenje formule 1, u kojoj L1 je neutralni ligand; X / X' su anjonski ligandi; R1 je -C1-5-alkil ili -C5-6-cikloalkil grupa; R2 je H, -C1-20-alkil, -C2-20-alkenil, -C2-20-alkinil ili aril grupa; R3 je -C1-6-alkil, -C1-6-alkoksi ili aril grupa, pri čemu je aril, u datom slučaju, supstituisan sa -C1-6-alkil ili -C1-6-alkoksi grupom; nje 0, 1, 2 ili 3.
2. Jedinjenje, prema zahtevu 1, formule la, u kojoj su L1, X, X', R1, R2, R3 i n, defmisani kao u zahtevu 1.
3. Jedinjenje, prema zahtevima 1 ili 2, pri čemu L1 je P(R11)3; R11 je -C1-6-alkil, -C3-8--cikloalkil ili aril grupa; ili L1 je ligand formule 6a, 6b, 6c ili 6d; R1 i R2 jesu svaki nezavisno H, -C1-20-alkil, -C2-20-alkenil ili fenil grupa, pri čemu je fenil, u datom slučaju, supstituisan sa do tri grupe nezavisno odabrane od -C1-6-alkil, -C1-6-alkoksi grupe ili halogena; R3 i R10 jesu svaki nezavisno H, -C1-20-alkil, -C2-20-alkenil ili fenil grupa, pri čemu je fenil, u datom slučaju, supstituisan sa do tri grupe nezavisno odabrane od -C1-6-alkil, -C1-6-alkoksi grupe ili halogena; ili se R3 i R10, zajedno sa atomima ugljenika za koje su vezani, povezuju obrazujući karbocikličan 3- do 8-člani prsten, Y i Y jesu halogen.
4. Jedinjenje, prema zahtevima l do 3, pri čemu R1 i R2, svaki nezavisno, jesu H, -C1-6-alkil, -C2-6-alkenil ili fenil grupa, pri čemu, u datom slučaju, fenil je supstituisan sa do tri grupe nezavisno odabrane od -C1-6-alkil, -C1-6-alkoksi grupe ili halogena; R3 i R10, svaki nezavisno, jesu H, -C1-6-alkil, -C2-6-alkenil ili fenil grupa, pri čemu, u datom slučaju, fenil je supstituisan sa do tri grupe nezavisno odabrane od -C1-6-alkil, -C1-6-alkoksi grupe ili halogena, ili se R3 i R10, zajedno sa atomima ugljenika za koje su vezani, povezuju obrazujući karbocikličan 5- do 7-člani prsten.
5. Jedinjenje, prema zahtevima l do 4, pri čemu 2 je H, -C1-6-alkil ili aril grupa; a svaki X i X'je halogen.
6. Jedinjenje, prema zahtevima l do 5, pri čemu L1 je PCy3 ili ligand formule 6a, 6b, 6c ili 6d; Cy je cikloheksil grupa; a svaki X i X'je hlor.
7. Jedinjenje, prema zahtevima l do 6, pri čemu L1 je ligand formule 6a, 6b, 6c ili 6d; a R1 i R2 jesu 2-metilfenil, 2, 6-dimetilfenil ili 2, 4, 6-trimetilfenil grupa.
8. Jedinjenje, prema zahtevima l do 7, pri čemu n je 0.
9. Jedinjenje, prema zahtevima l do 8, pri čemu R1 je 'Pr; R2 je H.
10. Jedinjenje formule 2, pri čemu R1 je -C1-5-alkil ili -C5-6-cikloalkil grupa; R2 je H, -C1-20-alkil, -C2-20-alkenil, -C2-20-alkinil ili aril grupa; R3 je -C1-6-alkil, -C1-6-alkoksi ili aril grupa, pri čemu aril može biti supstituisan sa -C1-6-alkil ili -C1-6-alkoksi grupom; R4 je -C1-20-alkil grupa; m je 0, 1 ili 2; a n je 0, 1, 2 or 3.
11. Jedinjenje, prema zahtevu 10, formule 2a, pri čemu su R1, R2, R3, R4, m i n, defmisani kao u zahtevu 10.
12. Jedinjenje, prema zahtevima 10 ili 11, pri čemu R2 je H, -C1-6-alkil ili aril grupa; R4 je -C1-6-alkil grupa; m je 0 ili 1.
13. Jedinjenje, prema zahtevima 10 do 12, pri čemu R4 je metil ili etil grupa; nje 0.
14. Jedinjenje, prema zahtevima 10 do 13, pri čemu R1 je izo-propil grupa; R2 je H; m je 0.
15. Postupak za proizvodnju kompleksa, prema bilo kojem od zahteva 1 do 9, pri čemu jedinjenje formule 2 ili 2a, prema zahtevima 10 do 14, reaguje sa rutenijumskim kompleksom opšte formule 5 pri čemu L1 i L2 su neutralni ligandi; R5 je H, -C1-20 -alkil, -C2-20-alkenil, -C2-2o-alkinil ili aril grupa; R6 je aril, vinil ili alenil grupa; X / X' su anjonski ligandi.
16. Postupak, prema zahtevu 15, koji se izvodi u prisustvu soli bakra.
17. Postupak za pripremanje intermedijera, formule 2 ili 2a, prema bilo kojem od zahteva 10 do 14, koji sačinjavaju stupnjevi sa reagensom formule RlZ (9) radi stvaranja intermedijera, formule 4, i b) reakcija intermedijera formule 4 sa reagensom za olefinaciju, formule uz stvaranje jedinjenja opšte formule 2, u kojoj su R1, R2, R3, R4, m i n, u formuli 2a, 3, 4, 9 i 10, definisani kao u zahtevima 10 do 14, a W je grupa koja se odvaja, pogodna za reakcije olefinacije; Z je halogen, -C1-6-alkil-S(O)2-, -C1-6-fluoroalkil-S(O)2-, aril-S(O)2 ili aril-S(0)3- grupa.
18. Postupak za metatezne reakcije, koji se sastoji u dovođenju u dodir sa katalizatorom, dva jedinjenja koja sadrže C=C duplu vezu, ili jednog jedinjenja koje sadrži najmanje dve C=C duple veze, pri čemu katalizator predstavlja rutenijumski kompleks, prema zahtevima l do 9.
19. Postupak za izvođenje metatezne reakcije zatvaranja prstena ili unakrsne metatezne reakcije, čiji postupak se sastoji u dovođenju u dodir nekog dialkenil jedinjenja sa rutenijumskim kompleksom, prema zahtevima l do 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL356652A PL199412B1 (pl) | 2002-10-15 | 2002-10-15 | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| PCT/EP2003/011222 WO2004035596A1 (en) | 2002-10-15 | 2003-10-10 | Ruthenium complexes as (pre)catalysts for metathesis reactions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MEP51508A MEP51508A (en) | 2011-02-10 |
| ME00345B true ME00345B (me) | 2011-05-10 |
Family
ID=32105755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2008-515A ME00345B (me) | 2002-10-15 | 2003-10-10 | Rutenijumski kompleksi kao (pred)-katalizatori metateznih reakcija |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6867303B2 (me) |
| EP (1) | EP1554294B1 (me) |
| JP (1) | JP4264418B2 (me) |
| KR (1) | KR101057963B1 (me) |
| CN (1) | CN1291996C (me) |
| AR (1) | AR041620A1 (me) |
| AT (1) | ATE332906T1 (me) |
| AU (1) | AU2003271713B2 (me) |
| BR (1) | BR0314856B1 (me) |
| CA (1) | CA2502342C (me) |
| CO (1) | CO5560614A2 (me) |
| DE (2) | DE60306795T2 (me) |
| DK (1) | DK1554294T3 (me) |
| EA (1) | EA008352B1 (me) |
| EC (1) | ECSP055653A (me) |
| ES (1) | ES2268412T3 (me) |
| HR (1) | HRP20050339B1 (me) |
| IL (1) | IL168002A (me) |
| ME (1) | ME00345B (me) |
| MX (1) | MXPA05003647A (me) |
| MY (1) | MY127285A (me) |
| NO (1) | NO335760B1 (me) |
| NZ (1) | NZ539944A (me) |
| PE (1) | PE20040510A1 (me) |
| PL (2) | PL199412B1 (me) |
| RS (1) | RS50334B (me) |
| TW (1) | TWI310768B (me) |
| UA (1) | UA79018C2 (me) |
| UY (1) | UY28020A1 (me) |
| WO (1) | WO2004035596A1 (me) |
| ZA (1) | ZA200501533B (me) |
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| 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 |
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