In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions
Yıl: 2011 Cilt: 35 Sayı: 5 Sayfa Aralığı: 699 - 709 Metin Dili: İngilizce İndeks Tarihi: 29-07-2022
In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions
Öz: Hydrogen-transfer reduction processes are attracting increasing interest from synthetic chemists in view of their operational simplicity. In the present study novel ruthenium carbene complexes were generated in situ and tested for their transfer hydrogenation reactions. The in situ prepared 3 component 1,3- dialkyltetrahydropyrimidinium salts (LHX)/[$RuCl_2(p-cymene)]_2$ and KOH catalyzed quantitatively the transfer hydrogenation of ketones under mild reaction conditions in 2-propanol.
Anahtar Kelime: Konular:
Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık
- 1. Gladali, S.; Alberico E. in: Transition Metals for Organic Synthesis, Eds.: Beller, M.; Bohm, C., Wiley-VCH, Weinheim, 2004.
- 2. Jiang, H.; Qiao, Q. D.; Gong, H. E. React. Kinet. Catal. L 1998, 65, 193-197.
- 3. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
- 4. Backvall, J. -E. J. Organomet. Chem. 2002, 652, 105-111.
- 5. Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300-1308.
- 6. Wang, W.; Li, Z.; Mu, W.; Su, L.; Wang, Q. Catal. Commun 2010, 11, 480-483.
- 7. Doucet, T.; Ohkuma, K.; Murata, T.; Yokozawa, M.; Kozawa, E.; Katayama, A. F.; England, T.; Ikariya, T.; Noyori, R. Angew. Chem. Int. Edit. 1998, 37, 1703-1707.
- 8. Sandoval, C. A.; Ohkuma, T.; Muniz, K.; Noyori, R. J. Am. Chem. Soc. 2003, 125, 13490-13503.
- 9. Noyori, R.; Yamakawa, M.; Hashiguchi, S. J. Org. Chem. 2001, 66, 7931-7944.
- 10. Poyatos, M.; Mata, J. A.; Falomir, E.; Crabtree, R. H.; Peris, E. Organometallics 2003, 22, 1110-114.
- 11. Danopoulos, A. A.; Winston, S.; Motherwell, W. B. Chem. Commun 2002, 1376-1378.
- 12. Louie, J.; Bielawski, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 11312-11313.
- 13. Noyori, R.; Okhuma, T. Angew. Chem. Int. Ed. 2001, 40, 40-73.
- 14. Okhuma, T.; Takeno, H.; Noyori, R. Adv. Synth. Catal 2001, 343, 369-375.
- 15. Dong, Z. R.; Li, Y. Y.; Chen, J. S.; Li, B. Z.; Xing, Y.; Gao, J. X. Org. Lett. 2005, 7, 1043-1045.
- 16. Bianchini, C.; Farnetti, E.; Glendenning, L.; Graziani, M.; Nardin, G.; Peruzzini, M.; Rocchini, E.; Zanobini, F. Organometallics. 1995, 14, 1489-1502.
- 17. Park, S.; Lough, A. J.; Morris, R. H. Inorg. Chem. 1996, 35, 3001-3006.
- 18. Kannan, S.; Kumar, K. N.; Ramesh, R. Polyhedron 2008, 27, 701708.
- 19. Clarke, M. L.; Diaz-Valenzuela, M. B.; Slawin, A. M. Z. Organometallics 2007, 26, 16-19.
- 20. Kagan, H. B.; Dang, T. P. J. Am. Chem. Soc 1972, 94, 6429-6433.
- 21. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc 1977, 99, 6262-6267.
- 22. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc 1980, 102, 7932-7934.
- 23. Fache, F.; Schulz, E.; Tommasino, M. L.; Lemaire, M. Chem. Rev., 2000, 100, 2159-2231.
- 24. Zhao, M.; Yu, Z.; Yan, S.; Li, Y. J. Organomet. Chem 2009, 694, 30683075.
- 25. Schlattera, A.; Woggon, W. -D. Adv. Synth. Catal 2008, 350, 995-1000.
- 26. Baratta, W.; Ballico, M.; Baldino, S.; Chelucci, G.; Herdtweck, E.; Siega, K.; Magnolia, S.; Rigo, P. Chem. Eur. J. 2008, 14, 9148-9160.
- 27. Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Schatte, G.; Stradiotto, M. Angew. Chem. Int. Ed. Engl. 2007, 46, 4732-4735.
- 28. Baratta, W.; Rigo, P. Eur. J. Inorg. Chem. 2008, 4041-4053.
- 29. Herrmann, W. A.; Elison, M.; Fischer, J.; Kocher, C.; Artus, G. R. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 2371-2374.
- 30. Herrmann, W. A. Angew. Chem. Int. Ed. Engl. 2002, 41, 1291-1309.
- 31. Mata, J. A.; Poyatos, M.; Peris, E. Coord. Chem. Rev. 2007, 251, 841-859.
- 32. Pugh, D.; Danopoulos, A. A. Coord. Chem. Rev. 2007, 251, 610-641.
- 33. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239-2246.
- 34. Gade, L. H.; Bellemin-Laponnaz, S. Coord. Chem. Rev. 2007, 251, 718-725.
- 35. Herrmann, W. A.; Weskamp, T.; Bohm, V. P. W. Adv. Organomet. Chem. 2001, 48, 1-69.
- 36. Huang, J.; Schanz, H. J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
- 37. Schwarz, J.; Bohm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrmann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773-1780.
- 38. Liddle, S. T.; Edworthy, I. S.; Arnold, P. L. Chem. Soc. Rev. 2007, 36, 1732-1745.
- 39. Kuhl, O. Chem. Soc. Rev. 2007, 36, 592-608.
- 40. Nolan, S. P. (Eds.: Nolan, S. P.), N-Heterocyclic Carbenes in Synthesis;Wiley: Weinheim, 2006.
- 41. Corberan, R.; Mas-Marza, E.; Peris, E. Eur. J. Inorg. Chem. 2009, 13, 1700-1716.
- 42. Hillier, A. C.; Lee, H. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 4246-4252.
- 43. Mas-Marza, E.; Poyatos, M.; Sanau, M.; Peris, E. Organometallics 2004, 23, 323-325.
- 44. Turkmen, H.; Pape, T.; Hahn, F. E.; Cetinkaya, B. Organometallics 2008, 27, 571-575.
- 45. Hahn, F. E.; Holtgrewe, C.; Pape, T.; Martin, M.; Sola, E.; Oro, L. A. Organometallics 2005, 24, 2203-2209.
- 46. Miecznikowski, J. R.; Crabtree, R. H. Organometallics 2004, 23, 629-631.
- 47. Albrecht, M.; Miecznikowski, J. R.; Samuel, A.; Faller, J.W.; Crabtree, R. H. Organometallics 2002, 21, 3596-3604.
- 48. Burling, S.; Whittlesey, M. K.; Williams, J. M. J. Adv. Synth. Catal 2005, 347,591-594.
- 49. Edwards, M. G.; Jazzar, R. F. R.; Paine, B. M.; Shermer, D. J.; Whittlesey, M. K.; Williams, J. M. J.; Edney, D. D. Chem. Commun 2004, 90-91.
- 50. Özdemir, İ.; Yaşar, S.; Çetinkaya, B. Transition Metal Chem. 2005, 30, 831-83
- 51. Kuhl, S.; Schneider, R.; Fort, Y. Organometallics 2003, 22, 41844186.
- 52. Mercan, D.; Çetinkaya, E.; Çetinkaya, B. J. Organomet. Chem. 2011, 696, 1359-1366.
- 53. Genet J. P. Acc. Chem. Res. 2003, 36, 908-918.
- 54. Johnstone, R. A. W.;Wilby, A. H.; Entwistle, I. D. Chem. Rev. 1985, 85, 129-170.
APA | ÖZCAN E, MERCAN D, GÜRBÜZ N, Çetinkaya E, ÇETİNKAYA B, Özdemir İ (2011). In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. , 699 - 709. |
Chicago | ÖZCAN Emine Özge,MERCAN Deniz,GÜRBÜZ Nevin,Çetinkaya Engin,ÇETİNKAYA Bekir,Özdemir İsmail In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. (2011): 699 - 709. |
MLA | ÖZCAN Emine Özge,MERCAN Deniz,GÜRBÜZ Nevin,Çetinkaya Engin,ÇETİNKAYA Bekir,Özdemir İsmail In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. , 2011, ss.699 - 709. |
AMA | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. . 2011; 699 - 709. |
Vancouver | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. . 2011; 699 - 709. |
IEEE | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ "In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions." , ss.699 - 709, 2011. |
ISNAD | ÖZCAN, Emine Özge vd. "In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions". (2011), 699-709. |
APA | ÖZCAN E, MERCAN D, GÜRBÜZ N, Çetinkaya E, ÇETİNKAYA B, Özdemir İ (2011). In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. Turkish Journal of Chemistry, 35(5), 699 - 709. |
Chicago | ÖZCAN Emine Özge,MERCAN Deniz,GÜRBÜZ Nevin,Çetinkaya Engin,ÇETİNKAYA Bekir,Özdemir İsmail In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. Turkish Journal of Chemistry 35, no.5 (2011): 699 - 709. |
MLA | ÖZCAN Emine Özge,MERCAN Deniz,GÜRBÜZ Nevin,Çetinkaya Engin,ÇETİNKAYA Bekir,Özdemir İsmail In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. Turkish Journal of Chemistry, vol.35, no.5, 2011, ss.699 - 709. |
AMA | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. Turkish Journal of Chemistry. 2011; 35(5): 699 - 709. |
Vancouver | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions. Turkish Journal of Chemistry. 2011; 35(5): 699 - 709. |
IEEE | ÖZCAN E,MERCAN D,GÜRBÜZ N,Çetinkaya E,ÇETİNKAYA B,Özdemir İ "In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions." Turkish Journal of Chemistry, 35, ss.699 - 709, 2011. |
ISNAD | ÖZCAN, Emine Özge vd. "In situ catalytic activities of 1,3-dialkyltetrahydropyrimidinium salts/[$RuCl_2(p-cymene)]_2$ system for transfer hydrogenation reactions". Turkish Journal of Chemistry 35/5 (2011), 699-709. |