pH-dependent catalytic activity and chemoselectivity in transfer hydrogenation catalyzed by iridium complex with 4,4′-dihydroxy-2,2′- bipyridine

Chemistry - A European Journal

Volumn 14, Issue 35, 2008, Pages 11076-11081

  Himeda, Yuichiro ^a   Onozawa Komatsuzaki, Nobuko ^a   Miyazawa, Satoru ^b   Sugihara, Hideki ^a   Hirose, Takuji ^b   Kasuga, Kazuyuki ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b SAITAMA UNIVERSITY   (Japan)

Author keywords

Ligand design; pH dependent catalyst; Substituent effects; Transfer hydrogenation; Water chemistry

Indexed keywords

ACIDS; ALDEHYDES; BIOCHEMISTRY; CARBONYLATION; CATALYSIS; CATALYST ACTIVITY; ELECTROCHEMICAL SENSORS; HYDROGENATION; IRIDIUM; IRIDIUM COMPOUNDS; KETONES; PH; PHENOLS; SELECTIVE CATALYTIC REDUCTION; UNSATURATED COMPOUNDS;

ACIDIC CONDITIONS; BASIC CONDITIONS; BIPYRIDINE; BOND REDUCTIONS; CATALYTIC ACTIVITIES; CHEMO SELECTIVITIES; CINNAMALDEHYDE; ELECTRONIC EFFECTS; HIGH ACTIVITIES; IRIDIUM CATALYSTS; IRIDIUM COMPLEXES; LIGAND DESIGN; PHENOLIC HYDROXYL GROUPS; SELECTIVE REDUCTIONS; SUBSTITUENT EFFECTS; TRANSFER HYDROGENATION; TRANSFER HYDROGENATIONS; TURNOVER FREQUENCIES; UNSATURATED CARBONYL COMPOUNDS; WATER CHEMISTRY;

PH EFFECTS;

EID: 57149123027     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801568     Document Type: Article

References (57)

1. B. Cornils, W. A. Herrmann, Aqueous-Phase Organometallic Cautlysis, Concepts and Applications. 2nd ed., Wiley-VCH, Weinheim, 2004.
2. S. Kobayashi, Adv. Synth. Catal. 2002, 344, 219.
3. F. Joó, Acc. Chem. Res. 2002, 35, 738-745.
4. X. F. Wu, X. G. Li, F. King, J. L. Xiao, Angew. Chem. 2005, 117, 3473-3477:
5. Angew. Chem. Int. Ed. 2005, 44, 3407-3411 .
6. C. A. Mebi, B. J. Frost, Organometallics 2005, 24, 2339-2346.
7. Y. Himeda, N. Onozawa-Komatsuzaki, H. Sugihara, H. Arakawa, K. Kasuga, J. Mol. Catal. A 2003, 195, 95-100.
8. J. Canivet, G. Labat, H. Stoeckli-Evans. G. Süss-Fink, Eur. J. Inorg. Chem. 2005, 4493-4500.
9. J. Canivet, G. Süss-Fink, Green Chem. 2007, 9, 391-397.
10. F. Joó, J. Kovács, A. C. Bényei, Á. Kathó, Angew. Chem. 1998, 110, 1024-1026;
11. Angew. Chem. Int. Ed. 1998, 37, 969-970.
12. F. Joó, J. Kovács, A.C. Bényei, Á. Kathó, Catal. Today 1998, 42, 441-448.
13. A. Rossin, G. Kovács, G. Ujaque, A. Lledós, F. Joó, Organometallics 2006, 25, 5010-5023.
14. G. Kovács, G. Ujaque, A. Lledós, F. Joó, Organometallics 2006, 25, 862-872.
15. X. F. Wu, J. L. Xiao, Chem. Commun. 2007, 2449-2466.
16. Y. Xing, J. S. Chen, Z. R. Dong, Y.Y. Li, J.X. Gao, Tetrahedron Lett. 2006, 47, 4501-4503.
17. J. S. Wu, F. Wang, Y. P. Ma, X. C. Cui, L. F. Cun, J. Zhu, J. G. Deng, B. L. Yu, Chem. Commun. 2006, 1766-1768.
18. D.S. Matharu, D.J. Morris, G.J. Clarkson, M. Wills, Chem. Commun. 2006, 3232-3234.
19. S. Zeror, J. Collin, J.C. Fiaud, L. A. Zouioueche, J. Mol. Catal. A 2006, 256, 85-89.
20. H. Y. Rhyoo, H. J. Park, Y. K. Chung, Chem. Commun. 2001, 2064-2065.
21. T Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300-1308.
22. A. J. Blacker, in Handbook of Homogeneous Hydrogénation, Vol. 3 (Eds.: J. G. De Vries, C.J. Elsevier), Wiley-VCH. Weinheim, 2007, pp. 1215-1244.
23. T. Zweifel, J. V. Naubron, T. Büttner, T. Ott, H. Grützmacher, Angew. Chem. 2008, 120, 3289-3293;
24. Angew. Chem. Int. Ed. 2008, 47, 3245-3249.
25. W. Baratta, G. Chelucci, E. Herdtweck, S. Magnolia, K. Siega, P. Rigo. Angew. Chem. 2007, 119, 7795-7798;
26. Angew. Chem. Int. Ed. 2007, 46, 7651-7654.
27. W. Baratta, G. Chelucci, S. Gladiali, K. Siega, M. Toniutti, M. Zanette, E. Zangrando, P. Rigo, Angew. Chem. 2005, 117, 6370-6375;
28. Angew. Chem. Int. Ed. 2005, 44, 6214-6219.
29. J. R. Miecznikowski, R. H. Crabtree. Organometallics 2004, 23, 629-631.
30. H. Yang, M. Alvarez, N. Lugan, R. Mathieu, J. Chem. Soc. Chem. Commun. 1995, 1721-1722.
31. X. F. Wu, J. K. Liu, X. H. Li, A. Zanotti-Gerosa, F. Hancock, D. Vinci, J. W. Ruan, J. L. Xiao, Angew. Chem. 2006, 118, 6870-6874;
32. Angew. Chem. Int. Ed. 2006, 45, 6718-6722.
33. J. B. Arterburn, M. Pannala, A. M. Gonzalez, R. M. Chamberlin, Tetrahedron Lett. 2000, 41, 7847-7849.
34. T. Doi, T. Fukuyama, J. Horiguchi, T. Okamura, I. Ryu. Synlett 2006, 721-724.
35. S. Sakaguchi, T. Yamaga. Y. Ishii, J. Org. Chem. 2001, 66, 4710-4712.
36. D. Xue, Y. C. Chen, X. Cui, Q. W. Wang, J. Zhu, J. G. Deng, J. Org. Chem. 2005, 70, 3584-3591.
37. S. Naskar, M. Bhaltacharjee, Tetrahedron Lett. 2007, 48, 465-467.
38. C. A. Mebi, R. P. Nair, B. J. Frost, Organometallics 2007, 26, 429-438.
39. Y. Himeda, N. Onozawa-Komatsuzaki, H. Sugihara, H. Arakawa, K. Kasuga, Abstr. Pap. The 50th Symposium on Coordination Chemistry of Japan. (Kusatsu, Japan) 2000, p. 280.
40. D. Westerhausen, S. Herrmann, W. Hummel, E. Sleckhan, Angew. Chem. 1992, 104, 1496-1498;
41. Angew. Chem. Int. Ed. Engl. 1992, 31, 1529-1531.
42. Y. Himeda, N. Onozawa-Komatsuzaki. H. Sugihara, H. Arakawa, K. Kasuga. Organometallics 2004, 23, 1480-1483.
43. Y. Himeda, Em. J. Inorg. Chem. 2007, 3927-3941.
44. Y. Himeda, N. Onozawa-Komatsuzaki. H. Sugihara, K. Kasuga. Organometallics 2007, 26, 702-712.
45. X. F. Wu, X. H. Li, A. Zanotti-Gerosa, A. Petlman, J. K. Liu, A. J. Mills, J. L. Xiao, Chem. Eur. J. 2008, 14, 2209-2222.
46. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
47. J. G. Muller, J. H. Acquaye, K.J. Takeuchi, Inorg. Chem. 1992, 31, 4552-4557.
48. X. Wu, C. Corcoran, S. Yang, J. Xiao, ChemSusChem 2008, 1, 71-74.
49. N. A. Cortez, G. Aguirre, M. Parra-Hake, R. Somanalhan, Tetraliedron: Asymmetry 2008, 19, 1304-1309.
50. S. Ogo, T. Abura, Y. Walanabe. Organometallics 2002, 21, 2964-2969.
51. T. Abura, S. Ogo, Y. Watanabe, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 4149-4154.
52. M. Ohba, K. Iizuka, H. Ishibashi, T Fujii, Tetrahedron 1997, 53, 16977-16986.
53. S. Ogo, R. Kabe, H. Hayashi, R. Harada, S. Fukuzumi, Dalton Trans. 2006, 4657-4663.
54. A. Gabrielsson, P. van Leeuwen, W. Kaim, Chem. Commun. 2006, 4926-4927.
55. S. Ogo, N. Makihara, Y. Watanabe, Organometallics 1999, 18, 5470-5474.
56. Y. R. Hong, C. B. Gorman, J. Org. Chem. 2003, 68, 9019-9025.
57. J. M. McFarland, M. B. Francis, J. Am. Chem. Soc. 2005, 127, 13490-13491.