Hydroxyapatite-supported palladium nanoclusters: A highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen

Journal of the American Chemical Society

Volumn 126, Issue 34, 2004, Pages 10657-10666

  Mori, Kohsuke ^a   Hara, Takayoshi ^a   Mizugaki, Tomoo ^a   Ebitani, Kohki ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; ALCOHOLS; CATALYSIS; ENERGY DISPERSIVE SPECTROSCOPY; HYDROXYAPATITE; OXIDATION; OXYGEN; PALLADIUM COMPOUNDS; SOLVENTS; STOICHIOMETRY; X RAY DIFFRACTION ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY;

MOLECULAR OXYGEN; NANOCLUSTERS; STOICHIOMETRIC HYDROXYAPATITE (HAP); TURNOVER FREQUENCY (TOF); TURNOVER NUMBER (TON); X-RAY ABSORPTION FINE STRUCTURES (XAFS);

NANOSTRUCTURED MATERIALS;

1 PHENYLETHANOL; ALCOHOL DERIVATIVE; CALCIUM; HYDROXYAPATITE; MONOMER; NANOPARTICLE; OXYGEN; PALLADIUM; PALLADIUM DICHLORIDE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CALCULATION; CATALYSIS; CATALYST; CATALYST SUPPORT; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENERGY DISPERSIVE X RAY ANALYSIS; INFRARED SPECTROSCOPY; OXIDATION; OXYGEN TENSION; PARTICLE SIZE; RECYCLING; STOICHIOMETRY; SURFACE PROPERTY; TECHNIQUE; TURNOVER TIME; X RAY ABSORPTION FINE STRUCTURE; X RAY ANALYSIS; X RAY DIFFRACTION; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 4344602894     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0488683     Document Type: Article

References (119)

1. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
2. (b) Hill, C. L. Advances in Oxygenated Processes, Baumstark, A. L., Ed.; JAI Press: London, 1988; Vol. 1, p 1.
3. (c) Hudlucky, M. Oxidations in Organic Chemistry; ACS Monograph Series; American Chemical Society: Washington, DC, 1990.
4. (d) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, U.K., 1991.
5. (e) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; John Wiley & Sons: New York, 1992.
6. (a) Cainelli, G.; Cardillo, G. Chromium Oxidants in Organic Chemistry; Springer: Berlin, 1984.
7. (b) Lee, D. G.; Spitzer, U. A. J. Org. Chem. 1970, 35, 3589.
8. (c) Menger, F. M.; Lee, C. Tetrahedron Lett. 1981, 22, 1655.
9. (a) Trost, B. M. Science 1991, 254, 1471.
10. (b) Anastas, P. T.; Warner, J. C. Green Chemistry, Theory and Practice; Oxford University Press: Oxford, U.K., 1998.
11. (c) Clark, J. H. Green Chem. 1999, 1, 1.
12. (d) Sheldon, R. A. Green Chem. 2000, 2, G1.
13. (e) Anastas, P. T.; Bartlett, L. B.; Kirchhoff, M. M.; Williamson, T. C. Catal. Today 2000, 55, 11.
14. (a) Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157.
15. (b) Gómez-Bengoa, E.; Noheda, P.; Echavarren, A. M. Tetrahedron Lett. 1994, 35, 7097.
16. (c) Aiet-Mohand, S.; Henin, F.; Muzart, J. Tetrahedron Lett. 1995, 36, 2473.
17. (d) Kaneda, K.; Fujii, M.; Morioka, K. J. Org. Chem. 1996, 61, 4502.
18. (e) Kaneda, K.; Fujie, Y.; Ebitani, K. Tetrahedron Lett. 1997, 38, 9023.
19. (f) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185.
20. (g) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
21. (h) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750.
22. (i) ten Brink, G.J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636.
23. (j) Stahl, S. S.; Thorman, J. L.; Nelson, R. C.; Kozee, M. A. J. Am. Chem. Soc. 2001, 123, 7188.
24. (k) Steinhoff, M. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
25. (l) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Adv. Synth. Catal. 2002, 344, 355.
26. (m) Steinhoff, B. A.; Stahl, S. S. Org. Lett. 2002, 4, 4179.
27. (n) Schultz, M. J.; Park, C. C.; Sigman, M. S. Chem. Commun. 2002, 3034.
28. (o) Jensen, D. R.; Schultz, M. J.; Mueller, J. A.; Sigman, M. S. Angew. Chem., Int. Ed. 2003, 42, 3810.
29. (a) Tang, R.; Diamond, S. E.; Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1978, 562.
30. (b) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786.
31. (c) Bäckvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473.
32. (d) Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishi, Y. Tetrahedron Lett. 1995, 36, 6923.
33. (e) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. I 1997, 3291.
34. (f) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661.
35. (g) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557.
36. (h) Coleman, K. S.; Lorber, C. Y.; Osborn, J. A. Eur. J. Inorg. Chem. 1998, 1673.
37. (i) Lee, M.; Chang, S. Tetrahedron Lett. 2000, 41, 7507.
38. (j) Shapley, P. A.; Zhang, N.; Allen, J. L.; Pool, D. H.; Liang, H.-C. J. Am. Chem. Soc. 2000, 122, 1079.
39. (k) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826.
40. (l) Csjernyik, G.: Ell, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
41. (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
42. (b) Markó, I. E.; Tsukazai, M.; Giles, P. R.; Brown, S. M.; Urch, C. J. Angew. Chem. Int. Ed. 1997, 36, 2208.
43. (c) Wang, Y.; Dubois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. Science 1998, 279, 537.
44. (d) Markó, I. E.; Gautier, A.; Chellé-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576.
45. (e) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Gautier, A.; Chellé-Regnaut, I.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433.
46. (f) Gamez, P.; Arends, I. W. C. E.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414.
47. Pd-catalyzed alcohol oxidation for kinetic resolution, see (a) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
48. (b) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
49. (c) Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202.
50. (d) Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63.
51. (e) Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835.
52. (f) Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600.
53. (g) Mueller, J. A.; Sigman, M. S. J. Am. Chem. Soc. 2003, 125, 7005.
54. (h) Mandal, S. K., Sigman, M. S. J. Org. Chem. 2003, 68, 7535.
55. Sheldon, R. A.; Wallau, M.; Arends, I. W. C. A.; Schuchardt, U. Acc. Chem. Res. 1998, 31, 485.
56. (a) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1, 1997, 1707.
57. (b) Vocanson, F.; Guo, Y. P.; Namy, J. L.; Kagan, H. B. Synth. Commun. 1998, 28, 2577.
58. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 67, 1750.
59. (d) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265.
60. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907.
61. (f) Choi, E.; Lee, C.; Na, Y.; Chang, S. Org. Lett. 2002, 4, 2369.
62. (g) Ji, H.-B.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2002, 43, 7179.
63. (h) Ji, H.-B.; Ebitani, K.; Mizugaki, T.; Kaneda, K. Catal. Commun. 2002, 3, 511.
64. (i) Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2002, 41, 4538.
65. (j) Zhan, B.-Z.; White, M. A.; Sham, T.-K.; Pincock, J. A.; Doucet, R. J.; Rao, K. V. R.; Robertson, K. N.; Cameron, T. S. J. Am. Chem. Soc. 2003, 125, 2195.
66. (k) Yamaguchi, K.; Mizuno, N. Chem. Eur. J. 2003, 9, 4353.
67. (l) Ciriminna, R.; Pagliaro, M. Chem. Eur. J. 2003, 9, 5067.
68. (m) Ebitani, K.; Ji, H.-B.; Mizugaki, T.; Kaneda, K. J. Mol. Catal. A: Chem. 2004, 212, 161.
69. Mallat, T.; Baiker, A. Catal. Today 1994, 19, 247.
70. Liotta, L. F.; Venezia, A. M.; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271.
71. (a) Nishimura, T.; Kakiuchi, N.; Inoue, M.; Uemura, S. Chem. Commun. 2000, 1245.
72. (b) Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6220.
73. (a) Ebitani, K.; Fujie, Y.; Kaneda, K. Langmuir 1999, 1907.
74. (b) Choi, K.-M.; Akita, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. New J. Chem. 2003, 27, 324.
75. (a) Uozumi, Y.; Nakao, R. Angew. Chem., Int. Ed. 2003, 42, 194.
76. (b) Corain, B.; Jerabek, K.; Centomo, P.; Canton, P. Angew. Chem., Int. Ed. 2004, 43, 959.
77. Elliott, J. C. Structure and Chemistry of the Apatites and Other Calcium Orthophosphates; Elsevier: Amsterdam, 1994.
78. (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144.
79. (b) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2001, 461.
80. (c) Mori, K.; Tano, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. New J. Chem. 2002, 26, 1536.
81. (d) Mori, K.; Yamaguchi, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2002, 124, 11572.
82. (e) Murata, M.; Hara, T.; Mori, K.; Ooe, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 4981.
83. (f) Hara, T.; Mori, K.; Ooe, M,; Mizugaki, T.; Ebitani, K.; Kaneda, K. Tetrahedron Lett. 2003, 44, 6207.
84. (g) Mori, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2003, 125, 11460.
85. Sugiyama, S.; Minami, T.; Hayashi, H.; Tanaka, M.; Shigemoto, N.; Moffat, J. B. J. Chem Soc., Faraday Trans. 1996, 92, 293.
86. See Supporting Information.
87. Tanaka, H.; Yasukawa, A.; Kandori, K.; Ishikawa, T. Colloids Surf. A 1997, 125, 53.
88. 2 (d = 47 Å) catalysts whose σ/d values were between 26% and 30%. See Figure S4 in Supporting Information.
89. (a) Schmid, G. Aspects of Homogeneous Catalysis; Ugo, R., Ed.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1990; Vol. 7, p 1.
90. (b) Benfield, R. E. J. Chem. Soc., Faraday Trans. 1992, 88, 1107.
91. (c) Veisz, B.; Király, Z.; Tóth, L.; Pécz, B. Chem. Mater. 2002, 14, 2882.
92. II center. See ref 16e.
93. Vollhardt, K. P. C.; Schore, N. E. Organic Chemistry, 2nd ed.; Freeman: New York, 1994; pp 924-929.
94. Arends, I. W. C. E.; Sheldon, R. A. Appl. Catal. A: Gen. 2001, 212, 175.
95. For example, see (a) Li, C.-J., Chan, T.-H., Eds. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
96. (b) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
97. (c) Manabe, K.; Kobayashi, S. Chem. Eur. J. 2002, 8, 4095.
98. d, weight of dried sample). The estimated hygroscopic degree of hydroxyapatite was 11.7.
99. Döbler, C.; Mehltretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447.
100. Cinnamyl alcohol was more unfavorable to be oxidized than benzyl alcohol in separate experiments (entries 1 and 11 in Table 3).
101. (a) Schmid, G. Chem. Rev. 1992, 92, 1709.
102. (b) Schimid, G.; Chi, L. F. Adv. Mater. 1998, 10, 515.
103. (c) Aiken, J. D.; Finke, R. G. J. Mol. Catal. A: Chem. 1999, 145, 1.
104. (d) Rao, C. N. R.; Kulkarni, G. U.; Thomas, P. J.; Edwards, P. P. Chem. Eur. J. 2002, 8, 29.
105. (a) Clusters and Colloids: From Theory to Applications; Schmid, G., Ed.; VCH: Weinheim, Germany, 1994.
106. (b) Nanoparticles and Nanostructured Films; Fendler, J. H., Ed.; Wiley-VCH: Weinheim, Germany, 1998.
107. (a) Teranishi, T.; Miyake, M. Chem. Mater. 1998, 10, 594.
108. (b) Teranishi, T.; Hosoe, M.; Tanaka, T.; Miyake, M. J. Phys. Chem. B 1999, 103, 3818.
109. Van Hardeveld, R.; Hartog, F. Surf. Sci. 1969, 15, 189.
110. LS. A similar approximation has been carried out in the studies of particle size effect on Heck and Suzuki coupling reactions. See refs 34b and 35.
111. (a) Augustine, R. L.; O'Leary, S. T. J. Mol. Catal. A: Chem. 1995, 95, 277.
112. (b) Le Bars, J.; Specht, U.; Bradley, J. S.; Blackmond, D. G. Langmuir 1999, 15, 7621.
113. Li, Y.; Boone, E.; EI-Sayed, M. A. Langmuir 2002, 18, 4921.
114. (a) Ozawa, F.; Ito, T.; Yamamoto, A. J. Am. Chem. Soc. 1980, 102, 6457.
115. (b) Noronha, G.; Henry, P. M. J. Mol. Catal. A 1997, 140, 75.
116. The distance between the center of a C=C bond and an oxygen atom of the O-H group of cinnamyl alcohol was calculated by the PM3 semiempirical method as implemented in MOPAC.
117. The single-site Pd catalysts oxidized both benzylic and aliphatic alcohols at almost similar reaction rates. See ref 4h.n.
118. 0 species by use of aryl halides with electron-withdrawing substituents and/or electron-donating phosphate ligands.
119. Tanaka, T.; Yamashita, H.; Tsuchitani, R.; Funabiki, T.; Yoshida, S. J. Chem. Soc., Faraday Trans. 1988, 84, 2987.