Selective hydrogen transfer reduction of ketones by recyclable ruthenium complex catalysts containing a 'ROMP polymer-attached' ligand

Journal of Molecular Catalysis A: Chemical

Volumn 245, Issue 1-2, 2006, Pages 152-160

  Nomura, Kotohiro ^a   Kuromatsu, Yutaka ^a  

^a NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Hydrogen transfer reduction; Polymer supported catalyst; Recyclable catalyst; ROMP; Ruthenium; Selective reduction

Indexed keywords

CATALYSTS; CHEMICAL COMPOUNDS; HYDROGEN; METHANOL; POLYMERS; REDUCTION; RUTHENIUM;

HYDROGEN TRANSFER REDUCTION; POLYMER SUPPORTED CATALYST; RECYCLABLE CATALYST; ROMP; SELECTIVE REDUCTION;

KETONES;

EID: 31544474579     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2005.09.047     Document Type: Article

References (59)

1. For example: T.W. Ford Polymeric Reagents and Catalysts ACS Symposium Series 308 American Chemical Society Washington, DC 1986 1
2. R.B. Merrifield Angew. Chem. 97 1985 801
3. Reviews concerning soluble polymer ligands: D.J. Gravert , and K.D. Janda Chem. Rev. 97 1997 489
4. P. Wentworth Jr., and K.D. Janda Chem. Commun. 1999 1917
5. P.H. Toy, and K.D. Janda Accounts Chem. Res. 33 2000 546
6. P.H. Toy, T.S. Reger, and K.D. Janda Aldrichmi. Acta 33 2000 87
7. C.W. Hartwig, D.J. Gravert, and K.D. Janda Chemtracs 12 1999 1
8. D.E. Bergbreiter Med. Res. Rev. 19 1999 439
9. D.E. Bergbreiter P.T. Anastas L.G. Heine T.C. Williamson Green Chemical Syntheses and Processes, ACS Symposium Series 767 American Chemical Society, Washington, DC 2000 182
10. D.E. Bergbreiter J. Polym. Sci. Part A: Polym. Chem. 39 2001 2351
11. S. Borman Chem. Eng. News June 4 2001 49
12. T.J. Dickerson, N.N. Reed, and K.D. Janda Chem. Rev. 102 2002 3325
13. D.E. Bergbreiter Chem. Rev. 102 2002 3345
14. For example (dendrimer): J.W.J. Knapen , A.W. van der Made , J.C. de Wilde , P.W.N.M. van Leeuwen , P. Wijkens , D.M. Grove , and G. van Koten Nature 372 1994 659
15. M.A. Hearshaw, and J.R. Moss Review Chem. Commun. 1999 1
16. R.M. Crooks, M. Zhao, L. Sun, V. Chechik, and L.K. Yeung Accounts Chem. Res. 34 2001 181
17. For example: D.E. Bergbreiter Catal. Today 42 1998 389
18. Use of ROMP polymer as the ligand, for example: M.R. Buchmeiser , and K. Wurst J. Am. Chem. Soc. 121 1999 11101
19. M.R. Buchmeiser Chem. Rev. 100 2000 1565
20. A.G.M. Barrett, B.T. Hopkins, and J. Kobberling Chem. Rev. 102 2002 3301
21. A.M. Harned, M. Zhang, P. Vedantham, S. Mukherjee, R.H. Herpel, D.L. Flynn, and P.R. Hanson Aldrichim. Acta 38 2005 3
22. Examples as the pioneering works: G.C. Bazan , E. Khosravi , R.R. Schrock , W.J. Feast , V.C. Gibson , M.B. O'Regan , J.K. Thomas , and W.M. Davis J. Am. Chem. Soc. 112 1990 8378
23. G.C. Bazan, J.H. Oskam, H. Cho, L.Y. Park, and R.R. Schrock J. Am. Chem. Soc. 113 1991 6899
24. For example: R.R. Schrock Y. Imamoglu Metathesis Polymerization of Olefins and Polymerization of Alkynes, NATO ASI Series 1998 Kluwer Academic Publishers pp. 1, 357
25. R.R. Schrock A. Fürstner Alkene Metathesis in Organic Synthesis 1998 Springer-Verlag Berlin Heidelberg 1
26. G.C. Bazan, R.R. Schrock, H. Cho, and V.C. Gibson Macromolecules 24 1991 4495
27. K. Nomura, S. Takahashi, and Y. Imanishi Macromolecules 34 2001 4712
28. J.J. Murphy, T. Kawasaki, M. Fujiki, and K. Nomura Macromolecules 38 2005 1075
29. K. Nomura, H. Ogura, and Y. Imanishi J. Mol. Catal. A 185 2002 311
30. K. Nomura Chem. Lett. 1991 1679
31. K. Nomura J. Mol. Catal. 73 1992 L1
32. K. Nomura J. Mol. Catal. A 95 1995 203
33. K. Nomura J. Mol. Catal. A 130 1998 1 (Review)
34. Part of these results have been previously presented: Y. Kuromatsu, M. Fujiki, and K. Nomura International Symposium on Catalysis and Fine Chemicals 2004 Hong Kong 2004 9
35. Examples for reviewing articles for (asymmetric) transfer hydrogenation; G. Zassinovich , G. Mestroni , and S. Gladiali Chem. Rev. 92 1992 1051
36. R. Noyori, and S. Hashiguchi Accounts Chem. Res. 30 1997 97
37. T. Naota, H. Takaya, and S.-I. Murahashi Chem. Rev. 98 1998 2599
38. M.J. Palmer, and M. Wills Tetrahedron Asymmetry 10 1999 2045
39. J.-E. Bäckvall J. Organomet. Chem. 652 2002 105
40. K. Everaere, A. Mortreux, and J.F. Carpentier Adv. Synth. Catal. 345 2003 67
41. H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, and M. Studer Adv. Synth. Catal. 345 2003 103
42. Selected examples for transfer hydrogenation of ketones; H. Doucet , T. Ohkuma , K. Murata , T. Yokozawa , M. Kozawa , E. Katayama , A.F. England , T. Ikariya , and R. Noyori Angew. Chem. Int. Ed. 37 1998 1703
43. M. Yamakawa, H. Ito, and R. Noyori J. Am. Chem. Soc. 122 2000 1466
44. K. Abdur-Rashid, S.E. Clapham, A. Hadzovic, J.N. Harvey, A.J. Lough, and R.H. Morris J. Am. Chem. Soc. 124 2002 15104
45. Recent examples for transfer hydrogenation in the presence of 2-(aminometyl)pyridine-phosphine ruhtnium(II) complexes, W. Baratta, E. Herdtweck, K. Siega, M. Toniutti, and P. Rigo Organometallics 24 2005 1660
46. Recent examples for (asymmetric) transfer hydrogenation of ketones using recyclable ruthenium catalysts; P.N. Liu , P.M. Gu , F. Wang , and Y.Q. Tu Org. Lett. 6 2004 169
47. S. Bastin, R.J. Eaves, C.W. Edwards, O. Ichihara, M. Whittaker, and M. Wills J. Org. Chem. 69 2004 5405
48. L. Della Ciena, W.J. Dressick, and A. von Zelewsky J. Heterocycl. Chem. 27 1990 163
49. L. Della Ciena, I. Hamachi, and T.J. Meyer J. Org. Chem. 54 1989 1731
50. 1H NMR spectra for the catalyst solution, recovered catalyst) are shown in the Supplementary data.
51. 1H NMR spectra and MALDI-TOF mass spectrometry.
52. For example, S. Komiya, and M. Hirano S. Komiya Synthesis of Organometallic Compounds: Practical Guide 1997 John Wiley and Sons Ltd. Baffins Lane, England 159
53. Reaction with norbornadiene, S.D. Robinson, and G. Wilkinson J. Chem. Soc. A 1965 843
54. Reaction with MeCN, D.J. Cole-Hamilton, and G. Wilkinson J. Chem. Soc. Dalton Trans. 1979 1283
55. This is due to the fact that a trace amount of polymer was lost during the filtration/precipitation process to recover the catalyst (ca. 39 mg) from the reaction mixture (total 50 mL).
56. w: 9639, 0.004 mmol (39 mg)] which we used in the first experiments, because the molecular weight for ring-opened poly(NBE) being much higher than those for others (ruthenium, etc.).
57. M.A. Bennett, and A.K. Smith J. Chem. Soc. Dalton Trans. 1974 233
58. G.C. Bazan, E. Khosravi, R.R. Schrock, W.J. Feast, V.C. Gibson, M.B. O'Reagan, J.K. Thomas, and W.M. Davis J. Am. Chem. Soc. 112 1990 8378
59. G.C. Bazan, J.H. Oskam, H. Cho, L.Y. Park, and R.R. Schrock J. Am. Chem. Soc. 113 1991 6899