pH-dependent transfer hydrogenation, reductive amination, and dehalogenation of water-soluble carbonyl compounds and alkyl halides promoted by Cp*Ir complexes

Organometallics

Volumn 20, Issue 23, 2001, Pages 4903-4910

  Ogo, Seiji ^a,b   Makihara, Nobuyuki ^b   Kaneko, Yuichi ^c   Watanabe, Yoshihito ^a,b,d  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

^c KOCHI UNIVERSITY   (Japan)

^d OKAZAKI INSTITUTE FOR INTEGRATIVE BIOSCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; CARBONYL COMPOUNDS; ELECTRON DONATING ABILITY; HYDRIDE COMPLEXES; LEWIS ACIDIC IRIDIUM IONS; ORGANOMETALLIC AQUA COMPLEXES; PH DEPENDENT TRANSFER HYDROGENATION; REDUCTIVE AMINATION;

CATALYSIS; COMPLEXATION; DEHALOGENATION; ELECTRONS; HYDROGENATION; IONS; MOLECULAR STRUCTURE; PH EFFECTS; REDUCTION; SOLUBILITY; WATER; X RAY ANALYSIS;

ORGANOMETALLICS;

EID: 0035851948     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010523v     Document Type: Article

References (57)

1. (a) Cornils, B. J. Mol. Catal. A 1999, 143, 1-20.
2. (b) Nomura, K. J. Mol. Catal. A 1998, 130, 1-28.
3. (c) Cornils, B.; Herrmann, W. A. In Aqueous-Phase Organometallic Catalysis; Wiley-VCH: Weinheim, Germany, 1998; p 615.
4. (d) Joó, F.; Kovács, J.; Kathó, Á.; Bényei, A. C.; Decuir, T.; Darensbourg, D. J. Inorg. Synth. 1998, 32, 1-45.
5. (e) Augé, J.; Beletskaya, I. P.; Cheprakov, A. V.; Fringuelli, F.; Gajewski, J. J.; Garner, P. P.; Grieco, P. A.; Kobayashi, S.; Lubineau, A.; Parker, D. T.; Piermatti, O.; Pizzo, F.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Thomson Science: London, 1998; p 310.
6. (f) Li, C.-J.; Chan, T-H. In Organic Reactions in Aqueous Media; Wiley: New York, 1997; p 199.
7. (g) Joó, F.; Kathó, Á. J. Mol. Catal. A 1997, 116, 3-26.
8. (h) Horváth, I. T.; Joó, F. In Aqueous Organometallic Chemistry and Catalysis; Kluwer Academic: Dordrecht, The Netherlands, 1995; p 317.
9. (i) Roundhill, D. M. Adv. Organomet. Chem. 1995, 38, 155-188.
10. (j) Chaloner, P. A.; Esteruelas, M. A.; Joó, F.; Oro, L. A. In Homogeneous Hydrogenation; Kluwer Academic: Dordrecht, The Netherlands, 1994; p 287.
11. (k) Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
12. (a) Joó, F.; Kovács, J.; Bényei, A. C.; Nádasdi, L.; Laurenczy, G. Chem. Eur. J. 2001, 7, 193-199.
13. (b) Kovács, J.; Todd, T. D.; Reibenspies, J. H.; Joó, F.; Darensbourg, D. J. Organometallics 2000, 19, 3963-3969.
14. (c) Tin, K.-C.; Wong, N.-B.; Li, R.-X.; Li, Y.-Z.; Hu, J.-Y.; Li, X.-J. J. Mol. Catal. A 1999, 137, 121-125.
15. (d) Joó, F.; Kovács, J.; Bényei, A. C.; Kathó, Á. Angew. Chem., Int. Ed. Engl. 1998, 37, 969-970.
16. (e) Joó, F.; Nádasdi, L.; Bényei, A. C.; Darensbourg, D. J. J. Organomet. Chem. 1996, 512, 45-50.
17. (a) Ogo, S.; Makihara, N.; Watanabe, Y. Organometallics 1999, 18, 5470-5474.
18. (b) Dadci, L.; Elias, H.; Frey, U.; Hörnig, A.; Koelle, U.; Merbach, A. E.; Paulus, H.; Schneider, J. S. Inorg. Chem. 1995, 34, 306-315.
19. (c) Makihara, N.; Ogo, S.; Watanabe, Y. Organometallics 2001, 20, 497-500.
20. (d) Poth, T.; Paulus, H.; Elias, H.; Ducker-Benfer, C.; Eldik, R. V. Eur. J. Inorg. Chem. 2001, 1361-1369.
21. (e) Cayemittes, S.; Poth, T.; Fernandez, M. J.; Lye, P. G.; Becker, M.; Elias, H.; Merbach, A. E. Inorg. Chem. 1999, 38, 4309-4316.
22. (f) Faure, M.; Vallina, A. T.; Stoeckli-Evans, H.; Süss-Fink, G. J. Organomet. Chem. 2001, 621, 103-108.
23. (g) Cayemittes, S.; Poth, T.; Fernandez, M. J.; Lye, P. G.; Becker, M.; Elias, H.; Merbach, A. E. Inorg. Chem. 1999, 38, 4309-4316.
24. (h) Lo, H. C.; Buriez, O.; Kerr, J. B.; Fish, R. H. Angew. Chem., Int. Ed. 1999, 38, 1429-1432.
25. (i) Mahon, M. F.; Whittlesey, M. K.; Wood, P. T. Organometallics 1999, 18, 4068-4074.
26. (j) Fidalgo, E. G.; Plasseraud, L.; Süss-Fink, G. J. Mol. Catal. A 1998, 132, 5-12.
27. (k) Egli, A.; Hegetschweiler, K.; Alberto, R.; Abram, U.; Schibli, R.; Hedinger, R.; Gramlich, V.; Kissner, R.; Schubiger, P. A. Organometallics 1997, 16, 1833-1840.
28. (l) Richens, D. T. In The Chemistry of Aqua Ions; Wiley: West Sussex, U.K., 1997; p 592.
29. (m) Ogo, S.; Chen, H.; Olmstead, M. M.; Fish, R. H. Organometallics 1996, 15, 2009-2013.
30. (n) Kölle, U.; Görissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911-917.
31. (o) Eisen, M. S.; Haskel, A.; Chen, H.; Olmstead, M. M.; Smith, D. P.; Maestre, M. F.; Fish, R. H. Organometallics 1995, 14, 2806-2812.
32. (p) Meister, G.; Rheinwald, G.; Stoeckli-Evans, H.; Süss-Fink, G. J. Chem. Soc., Dalton Trans. 1994, 3215-3223.
33. (q) Koelle, U. Coord. Chem. Rev. 1994, 135/136, 623-650.
34. (a) Darensbourg, D. J.; Stafford, N. W.; Joó, F.; Reibenspies, J. H. J. Organomet. Chem. 1995, 488, 99-108.
35. (b) Darensbourg, D. J.; Joó, F.; Kannisto, M.; Kathó, Á.; Reibenspies, J. H.; Daigle, D. J. Inorg. Chem. 1994, 33, 200-208.
36. (c) Darensbourg, D. J.; Joó, F.; Kannisto, M.; Kathó, Á.; Reibenspies, J. H. Organometallics 1992, 11, 1990-1993.
37. (d) Bényei, A.; Joó, F. J. Mol. Catal. 1990, 58, 151-163.
38. (a) Chandrasekhar, S.; Reddy, C. R.; Ahmed, M. Synlett 2000, 11, 1655-1657.
39. (b) Zimmermann, B.; Herwig, J.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 2372-2375.
40. (c) Schaffrath, H.; Keim, W. J. Mol. Catal. A 1999, 140, 107-113.
41. (a) Bényei, A. C.; Lehel, S.; Joó, F. J. Mol. Catal. A 1997, 116, 349-354.
42. (b) Rajagopal, S.; Spatola, A. F. J. Org. Chem. 1995, 60, 1347-1355.
43. (c) Marques, C. A.; Selva, M.; Tundo, P. J. Org. Chem. 1995, 60, 2430-2435.
44. (d) Ram, S.; Ehrenkaufer, R. E. Synthesis 1988, 91-95.
45. 6) have been deposited with the Cambridge Crystallographic Data Center as Supplementary Publication Nos. CCDC-165018, CCDC-165019, CCDC-165020, CCDC-165021, and CCDC-165022, respectively. Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB21EZ, U.K. (fax, (+44)-1223-336-033; e-mail, deposit@ccdc.cam.ac.uk).
46. w = 0.051.
47. w = 0.088.
48. pD = pH meter reading + 0.4: Glasoe, P. K.; Long, F. A. J. Phys. Chem. 1960, 64, 188-190.
49. 4 acid, sodium salt.
50. The hydroxo complexes 5-7 are catalytically inactive for the reductions in this study.
51. Nutton, A.; Bailey, P. M.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1981, 1997-2002.
52. w = 0.117.
53. 2O reveals hydrogen bonds between the aqua ligand of 7 and the waters of crystallization.
54. w = 00.092.
55. Shimadzu gas chromatograph, GC-8A with Unibeads C.
56. Hollmann, F.; Schmid, A.; Steckhan, E. Angew. Chem., Int. Ed. 2001, 40, 169-171.
57. 3CN at pH 6-8: Lane, C. F. Synthesis 1975, 135-146.