Highly dispersed ruthenium hydroxide supported on titanium oxide effective for liquid-phase hydrogen-transfer reactions

Chemistry - A European Journal

Volumn 14, Issue 36, 2008, Pages 11480-11487

  Yamaguchi, Kazuya ^a   Koike, Takeshi ^a   Kim, Jung Won ^a   Ogasawara, Yoshiyuki ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alcohols; Carbonyl compounds; Heterogeneous catalysis; Racemization; Reduction

Indexed keywords

ABSORPTION SPECTROSCOPY; ALUMINUM; CARBONYLATION; CATALYSIS; CATALYST ACTIVITY; CATALYST SUPPORTS; CATALYSTS; COORDINATION REACTIONS; ELECTROCHEMICAL SENSORS; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTROSLAG REMELTING; HYDROGEN; OXIDE MINERALS; PHOTOELECTRON SPECTROSCOPY; REACTION RATES; RUTHENIUM; RUTHENIUM COMPOUNDS; SPIN DYNAMICS; TITANIUM; TITANIUM DIOXIDE; TITANIUM OXIDES; X RAY ANALYSIS;

ABSORPTION FINE STRUCTURES; ALLYLIC ALCOHOLS; BET SURFACES; CARBONYL COMPOUNDS; CATALYTIC ACTIVITIES; CATALYTIC PERFORMANCES; CHIRAL SECONDARY ALCOHOLS; COORDINATION NUMBERS; ELECTRON SPIN RESONANCES; HETEROGENEOUS CATALYSIS; HETEROGENEOUS CATALYSTS; MONOMERIC SPECIES; MONOTONICALLY; RACEMIZATION; TRANSFER REACTIONS; X-RAY DIFFRACTIONS; X-RAY PHOTOELECTRON SPECTROSCOPIES;

X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 57649171456     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200801655     Document Type: Article

References (70)

1. a) R. A. Sheldon, H. van Bekkum, Fine Chemical through Heterogeneous Catalysis, Wiley, Weinheim, 2001;
2. b) G. Centi, F. Cavani, F. Trifiro, Selective Oxidation by Heterogeneous Catalysis, Kluwer, New York, 2001;
3. c) I. V. Kozhevnikov, NATO Science Series, II: Mathematics, Physics and Chemistry, Kluwer, New York, 2003, pp. 351-380;
4. d) B. Warren, S. T. Oyama, Heterogeneous Hydrocarbon Oxidation, ACS, Washington, D. C., 1996;
5. e) A. Bhan, E. Iglesia, Acc. Chem. Res. 2008, 41, 559.
6. K. Yamaguchi, T. Koike, M. Kotani, M. Matsushita, S. Shinachi, N. Mizuno, Chem. Eur. J. 2005, 11, 6574.
7. J. W. Kim, T. Koike, M. Kotani, K. Yamaguchi, N. Mizuno, Chem. Eur. J., 2008, 14, 4104.
8. a) K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. 2004, 116, 1602;
9. Angew. Chem. Int. Ed. 2004, 43, 1576;
10. b) K. Yamaguchi, N. Mizuno, Angew. Chem. 2003, 115, 1517;
11. Angew. Chem. Int. Ed. 2003, 42, 1479;
12. c) K. Yamaguchi, N. Mizuno, Chem. Eur. J. 2003, 9, 4353;
13. d) K. Yamaguchi, N. Mizuno, Angew. Chem. 2002, 114, 4720;
14. Angew. Chem. Int. Ed. 2002, 41, 4538.
15. a) H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N. Mizuno, Angew. Chem. 2007, 119, 5294;
16. Angew. Chem. Int. Ed. 2007, 46, 5202;
17. b) H. Fujiwara, Y. Ogasawara, M. Kotani, K. Yamaguchi, N. Mizuno, Chem. Asian J. 2008, 3, 1715.
18. a) R. A. Sheldon, Chirotechnology, Industrial Synthesis of Optically Active Compounds, Dekker, New York, 1993;
19. b) C. H. Wang, G. M. Whitesides, Enzymes in Synthetic Organic Chemistry, Elsevier, Amsterdam, 1994.
20. a) H. Meerwein, R. Schmidt, Justus Liebigs Ann. Chem. 1925, 444, 221;
21. b) A. Verley, Bull. Soc. Chim. Fr. 1925, 37, 537;
22. c) W. Ponndorf, Angew. Chem. 1926, 39, 138;
23. d) K. Nishida, M. Noda, Chirality 2002, 14, 759;
24. e) J. F. de Graauw, J. A. Peters, H. van Bekkum, J. Huskens, Synthesis 1994, 1007;
25. f) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 1992, 92, 1051;
26. g) T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599;
27. h) J.-E. Bäckvall, R. L. Chowdhury, U. Karlsson, J. Chem. Soc. Chem. Commun. 1991, 473;
28. i) A. Aranyos, G. Csjernyik, K. J. Szabó, J.-E. Bäckvall, Chem. Commun. 1999, 351;
29. j) R. Noyori, Chem. Soc. Rev. 1989, 18, 187;
30. k) R. Noyori, Science 1990, 248, 1194;
31. l) R. Noyori, H. Takaya, Ace. Chem. Res. 1990, 23, 345;
32. m) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97;
33. n) M. J. Palmer, M. Will, Tetrahedron: Asymmetry 1999, 10, 2045.
34. a) B. A. Persson, A. L. E. Larsson, M. Le Ray, J.-E. Bäckvall, J. Am. Chem. Soc. 1999, 121, 1645;
35. b) O. Pàmies, A. H. Éll, J. S. M. Samec, N. ll, J. S. M. Samec, N. Hermanns, J.-E. Bäckvall, Tetrahedron Lett. 2002, 43, 4699;
36. c) O. Pàmies, J.-E. Bäckvall, J. Org. Chem. 2002, 67, 1261;
37. d) J. H. Koh, H. M. Jung, M.-J. Kim, J. Park, Tetrahedron Lett. 1999, 40, 6281;
38. e) J. H. Choi, Y. H. Kim, S. H. Nam, S. T. Shin, M.-J. Kim, J. Park, Angew. Chem. 2002, 114, 2479;
39. Angew. Chem. Int. Ed. 2002, 41, 2373;
40. f) M.-J. Kim, Y. Chung, Y. K. Choi, H. K. Lee, D. Kim, J. Park, J. Am. Chem. Soc. 2003, 125, 11494;
41. g) R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656;
42. h) P. M. Dinh, J. A. Howarth, A. R. Hudnott, J. M. J. Williams, W. Harris, Tetrahedron Lett. 1996, 37, 7623;
43. i) A. Dijksman, J. M. Elzinga, Y.-X. Li, I. W. C. E. Arends, R. A. Sheldon, Tetrahedron: Asymmetry 2002, 13, 879;
44. j) M. Ito, A. Osaku, S. Kitahara, M. Hirakawa, T. Ikariya, Tetrahedron Lett. 2003, 44, 7521.
45. V. Cadierno, J. Francos, J. Gimeno, N. Nebra, Chem. Commun. 2007, 2536.
46. a) A. N. Parvulescu, P. A. Jacobs, D. E. De Vos, Adv. Synth. Catal. 2008, 350, 113;
47. b) S. Wuyts, J. Wahlen, P. A. Jacobs, D. E. De Vos, Green Chem 2007, 9, 1104;
48. c) A. N. Parvulescu, P. A. Jacobs, D. E. De Vos, Chem. Eur. J. 2007, 13, 2034;
49. d) S. Wuyts, K. De Temmer-man, P. A. Jacobs, D. E. De Vos, Chem. Eur. J. 2007, 13, 2034;
50. e) Á. Zsigmond, A. Kecskeméti, K. Bogár, F. Notheisz, E. Mernyák, Catal. Commun. 2005, 6, 520;
51. f) M. T. Reetz, K. Schimossek, Chimia 1996, 50, 668;
52. g) S. Wuyts, K. De Temmerman, D. E. De Vos, P. A. Jacobs, Chem. Commun. 2003, 1928;
53. h) W.-H. Kim, R. Karvembu, J. Park, Bull. Korean Chem Soc. 2004, 25, 931;
54. i) S. Wuyts, D. E. De Vos, F. Verpoort, D. Depla, R. De Gryse, P. A. Jacobs, J. Catal. 2003, 219, 417.
55. a) D. Briggs, M. P. Seah, Practical Surface Analysis by Auger and X-ray Photoelectron Spectroscopy, Wiley, Chichester, 1983;
56. b) G. P. Williams in CRC Handbook of Chemistry and Physics, 82nd Edition (Eds.: D. R. Lida), CRC Press, Washington DC, 2001, Section 10, pp. 200-205.
57. a) K.-H. Chang, C.-C. Hu, J. Eledrochem. Soc. 2004, 151, A958;
58. b) G. E. De Benedetto, M. R. Guascito, R. Ciriello, T. R. I. Cataldi, Anal. Chim. Acta 2000, 410, 143;
59. c) H. Y. H. Chan, C. G. Takoudis, M. J. Weaver, J. Catal. 1997, 172, 336;
60. d) C. D. Wager, D. A. Zatko, R. H. Raymond, Anal. Chem. 1980, 52, 1445.
61. 6 octahedra (Figure 3a). The octahedra are linked in chains along the c axis by sharing two oxygen atoms with each of two neighboring octahedra. The Ru-Ru distance of neighboring octahedra along these chains is 3.107 Å. Each octahedral chain links to four neighboring chains by sharing oxygen atoms to form a three-dimensional network to create eight Ru-Ru distances at 3.535 Å: P. Triggs, Helv. Phys. Acta 1985, 58, 657.
62. a) D. A. McKeown, P. L. Hagans, L. P. L. Carette, A. E. Russell, K. E. Swider, D. R. Rolison, J. Phys. Chem. B 1999, 103, 4825;
63. b) B.-Z. Zhan, M. A. White, T.-K. Sham, X. A. Pincock, R. J. Doucet, K. V. R. Rao, K. N. Robertson, T. S. Cameron, J. Am. Chem. Soc. 2003, 125, 2195.
64. a) G.-D. Lei, L. Kevan, J. Phys. Chem. 1991, 95, 4506;
65. b) P. J. Carl, S. C. Larsen, J. Catal. 2000, 196, 352.
66. 3+ species: a) M. Fabre, J. Jaud, M. Hliwa, J.-P. Launay, J. Bonvosin, Inorg. Chem. 2006, 45, 9332;
67. b) O. Schiemann, N. J. Turro, J. K. Barton, J. Phys. Chem. B 2000, 104, 7214.
68. The possible reaction mechanisms are shown in Schemes S2-S4 in the Supporting Information.
69. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
70. Purification of Laboratory Chemicals, 3rd edition (Eds.: D. D. Perrin, W. L. F. Armarego), Pergamon, Oxford, 1988.