Zinc(II) containing γ-keggin sandwich-type silicotungstate: Synthesis in organic media and oxidation catalysis

Angewandte Chemie - International Edition

Volumn 49, Issue 35, 2010, Pages 6096-6100

  Kikukawa, Yuji ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alcohols; Homogeneous catalysis; Oxidation; Polyoxometalates; Zinc

Indexed keywords

CHEMO-SELECTIVITY; HOMOGENEOUS CATALYSIS; ORGANIC MEDIA; OXIDATION CATALYSIS; POLYOXOMETALATES; QUANTITATIVE YIELDS; SECONDARY ALCOHOLS;

ACETONE; CATALYSIS; OXIDATION; REACTION KINETICS; TUNGSTEN; ZINC COMPOUNDS;

ZINC;

EID: 77956044090     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201001468     Document Type: Article

References (71)

1. C. L. Hill, C. M. Prosser-McCartha, Coord. Chem. Rev. 1995, 143, 407;
2. T. Okuhara,N. Mizuno,M. Misono, Adv. Catal. 1996, 41, 113;
3. R. Neumann, Prog. Inorg. Chem. 1998, 47, 317;
4. Thematic issue on polyoxometalates. (Ed. C. L. Hill) Chem. Rev. 1998, 98, 1-390;
5. I. V. Kozhevnikov, Catalysis by Polyoxometalates, Wiley, Chichester, 2002.
6. A. Tézé, G. Hervé, Inorg. Synth. 1990, 27, 85.
7. Y. Nakagawa, K. Kamata, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. 2005, 117, 5266;
8. Angew. Chem. Int. Ed. 2005, 44, 5136;
9. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, N. Mizuno, Angew. Chem. 2008, 120, 2441;
10. Angew. Chem. Int. Ed. 2008, 47, 2407;
11. Y. Kikukawa, S. Yamaguchi, Y. Nakagawa, K. Uehara, S. Uchida, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 2008, 130, 15872.
12. A. Tézé, M. Michelon, G. Hervé, Inorg. Chem. 1997, 36, 5666;
13. B. Botar, P. Kögerler, C. L. Hill, Inorg. Chem. 2007, 46, 5398;
14. A. Sartorel, M. Carraro, G. Scorrano, R. De Zorzi, S. Geremia, N. D. McDaniel, S. Bernhard, M. Bonchio, J. Am. Chem. Soc. 2008, 130, 5006;
15. Y. Kikukawa, S. Yamaguchi, K. Tsuchida, Y. Nakagawa, K. Uehara, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 2008, 130, 5472;
16. B. S. Bassil, S. S. Mal, M. H. Dickman, U. Kortz, H. Oelrich, L. Walder, J. Am. Chem. Soc. 2008, 130, 6696;
17. Y. V. Geletii, B. Botar, P. Kögerler, D. A. Hillesheim, D. G. Musaev, C. L. Hill, Angew. Chem. 2008, 120, 3960;
18. Angew. Chem. Int. Ed. 2008, 47, 3896.
19. U. Kortz, Y. P. Jeannin, A. Tézé, G. Hervé, S. Isber, Inorg. Chem. 1999, 38, 3670;
20. U. Kortz, S. Isber, M. H. Dickman, D. Ravot, Inorg. Chem. 2000, 39, 2915;
21. F. Hussain, B. S. Bassil, L.-H. Bi, M. Reicke, U. Kortz, Angew. Chem. 2004, 116, 3567;
22. Angew. Chem. Int. Ed. 2004, 43, 3485;
23. L. Lisnard, P. Mialane, A. Dolbecq, J. Marrot, J. M. Clemente-Juan, E. Coronado, B. Keita, P. de Oliveira, L. Nadjo, F. Sécheresse, Chem. Eur. J. 2007, 13, 3525;
24. Z. Luo, P. Kögerler, R. Cao, I. Hakim, C. L. Hill, Dalton Trans. 2008, 54;
25. S. G. Mitchell, C. Ritchie, D.-L. Long, L. Cronin, Dalton Trans. 2008, 1415;
26. U. Kortz, S. Matta, Inorg. Chem. 2001, 40, 815;
27. Z. Zhang, Y. Li, E. Wang, X. Wang, C. Qin, H. An, Inorg. Chem. 2006, 45, 4313.
28. B. S. Bassil, M. H. Dickman, M. Reicke, U. Kortz, B. Keita, L. Nadjo, Dalton Trans. 2006, 4253;
29. H. Liu, J. Peng, Z. Su, Y. Chen, B. Dong, A. Tian, Z. Han, E. Wang, Eur. J. Inorg. Chem. 2006, 4827.
30. 2+ ions) generally prefer to exist as monomeric species in aqueous media: a) D. T. Richens, The Chemistry of Aqua Ions,Wiley, Chichester, 1997;
31. C. F. Base, Jr., R. E. Mesmer, The Hydrolysis of Cations, Wiley, New York, 1976.
32. K. Kamata, K. Yonehara, Y. Sumida, K. Yamaguchi, S. Hikichi, N. Mizuno, Science 2003, 300, 964;
33. K. Kamata, M. Kotani, K. Yamaguchi, S. Hikichi, N. Mizuno, Chem. Eur. J. 2007, 13, 639;
34. R. Ishimoto, K. Kamata, N. Mizuno, Angew. Chem. 2009, 121, 9062;
35. Angew. Chem. Int. Ed. 2009, 48, 8900.
36. 2 by tungsten-based catalysts preferentially gives the epoxy alcohol 1c rather than the enone 1b: a) D. Prat, B. Delpech, R. Lett, Tetrahedron Lett. 1986, 27, 711;
37. Y. Ishii, K. Yamawaki, T. Ura, H. Yamada, T. Yoshida, M. Ogawa, J. Org. Chem. 1988, 53, 3587;
38. A. L. Villa de P. , B. F. Sels, D. E. De Vos, P. A. Jacobs, J. Org. Chem. 1999, 64, 7267;
39. K. Sato, M. Aoki, M. Ogawa, T. Hashimoto, D. Panyella, R. Noyori, Bull. Chem. Soc. Jpn. 1997, 70, 905.
40. [10b] similar in-situ-prepared catalysts in organic media have not been reported to our knowledge: a) I. A. Weinstock, E. M. G. Barbuzzi, M.W. Wemple, J. J. Cowan, R. S. Reiner, D. M. Sonnen, R. A. Heintz, J. S. Bond, C. L. Hill, Nature 2001, 414, 191;
41. D. Sloboda-Rozner, P. L. Alster, R. Neumann, J. Am. Chem. Soc. 2003, 125, 5280.
42. Transition-metal-substituted POMs have usually been synthesized by the reaction of alkali-metal salts of lacunary POMs and the corresponding transition-metal salts in aqueous media. To date, there are only a few reports on the synthesis in organic media. The strategy to use organic media and to control the reactivities of POMs with counter cations demonstrated herein will open up a new avenue for POM chemistry: a) A. M. Khenkin, L. J.W. Shimon, R. Neumann, Eur. J. Inorg. Chem. 2001, 789;
43. K. Yamaguchi, N. Mizuno, New J. Chem. 2002, 26, 972;
44. P. Mialane, C. Duboc, J. Marrot, E. Rivière, A. Dolbecq, F. Sécheresse, Chem. Eur. J. 2006, 12, 1950.
45. 2] complex in aqueous medium. They mentioned that the choice of the chromium precursor was crucial for the synthesis: J.-D. Compain, P. Mialane, A. Dolbecq, I. M. Mbomekallé, J. Marrot, F. Sécheresse, C. Duboc, E. Rivière, Inorg. Chem. 2010, 49, 2851.
46. CCDC-768702 (TBA-Zn4) contains the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif. It was confirmed by IR measurements that TBA-Zn4 was thermally stable upon the heat treatment at least up to 80°C.
47. T. J. R. Weakley, J. Chem. Soc. Dalton Trans. 1973, 341;
48. J. Wang, L. Yan, G. Li, X. Wang, Y. Ding, J. Suo, Tetrahedron Lett. 2005, 46, 7023;
49. M. Piepenbrink, E. M. Limanski, B. Krebs, Z. Anorg. Allg. Chem. 2002, 628, 1187;
50. C. M. Tourné, G. F. Tourné, F. J. Zonnevijlle, J. Chem. Soc. Dalton Trans. 1991, 143;
51. R. Neumann, A. M. Khenkin, Inorg. Chem. 1995, 34, 5753;
52. R. Neumann, A. M. Khenkin, J. Mol. Catal. 1996, 114, 169;
53. U. Kortz, N. K. Al-Kassem,M. G. Savelieff, N. A. Al Kadi, M. Sadakane, Inorg. Chem. 2001, 40, 4742;
54. D. Drewes, E. M. Limanski, B. Krebs, Eur. J. Inorg. Chem. 2005, 1542;
55. H. Tan, Z. Zhang, D. Liu, Y. Qi, E.Wang, Y. Li, J. Cluster Sci. 2008, 19, 543;
56. M. Kozik, L. C.W. Baker, J. Am. Chem. Soc. 1987, 109, 3159;
57. S.-T. Zheng, J. Zhang, G.-Y. Yang, Eur. J. Inorg. Chem. 2004, 2004.
58. J. Tao, M.-L. Tong, J.-X. Shi, X.-M. Chen, S. W. Ng, Chem. Commun. 2000, 2043;
59. M. Alexiou, E. Katsoulakou, C. Dendrinou-Samara, C. P. Raptopoulou, V. Psycharis, E. Manessi- Zoupa, S. P. Perlepes, D. P. Kessissoglou, Eur. J. Inorg. Chem. 2005, 1964.
60. 2 (air) as a sole oxidant: a) R. A. Sheldon, I.W. C. E. Arends, D. Dijisman, Catal. Today 2000, 57, 157;
61. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037;
62. T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J. 2008, 3, 196.
63. 2 could be the oxidant of choice for alcohol oxidations (especially for fine chemicals): R. A. Sheldon, J. Chem. Technol. Biotechnol. 1997, 68, 381, and see also ref. [16a].
64. The TBA-Zn4-catalyzed oxidation of benzyl alcohol under the conditions described in Table 2 gave benzaldehyde and benzoic acid in 87% and 3% yields (for 2.5 h), respectively.
65. Acetone was not a special solvent; for example, the oxidation of 1a in acetonitrile gave 1b in > 99% yield under the same conditions.
66. 2 with respect to alcohols (other conditions were the same as those described in Table 2) gave the corresponding ketones in 99%(for 2 h), 94%(for 3 h), and 93% (for 4.5) yields, respectively.
67. 2+) show high chemoselectivity to alcoholic functions: a) J. Wang, L. Yan, G. Qian, S. Li, K. Yang, H. Liu, X.Wang, Tetrahedron 2007, 63, 1832;
68. J.Wang, L. Yan, G. Li, X.Wang, Y. Ding, J. Suo, Tetrahedron Lett. 2007, 46, 7023;
69. G. Maayan, R. H. Fish, R. Neumann, Org. Lett. 2003, 5, 3547.
70. [16]
71. 2] (1.6 mol%), and TBABr (6.4 mol%). These results can rule out any contribution to the observed catalysis from tungsten- and/or zinc-based impurities, and the observed catalysis is intrinsically derived from TBAZn4.