Controlled synthesis of hydroxyapatite-supported palladium complexes as highly efficient heterogeneous catalysts

Journal of the American Chemical Society

Volumn 124, Issue 39, 2002, Pages 11572-11573

  Mori, Kohsuke ^a   Yamaguchi, Kazuya ^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

HYDROXYAPATITE; PALLADIUM COMPLEX;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; SYNTHESIS;

CATALYSIS; FOURIER ANALYSIS; HYDROXYAPATITES; ORGANOMETALLIC COMPOUNDS; PALLADIUM; SPECTROMETRY, X-RAY EMISSION;

EID: 0037010004     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja020444q     Document Type: Article

References (33)

1. (a) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: London, 1985.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
3. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
4. (d) Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, 1996.
5. (e) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
6. (a) Gates, B. C. Chem. Rev. 1995, 95, 511.
7. (b) Basset, J.-M.; Lefebre, F.; Santini, C. Coord. Chem. Rev. 1998, 178-180, 1703.
8. (c) Iwasawa, Y. Prepr. Solid Catal. 1999, 427.
9. (d) Bergbreiter, D. E. Med. Res. Rev. 1999, 19, 439.
10. (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144.
11. (b) Mori, K.; Yamaguchi, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2001, 461.
12. Sugiyama, S.; Minami, T.; Hayashi, H.; Tanaka, M.; Shigemoto, N.; Moffat, J. B. J. Chem Soc., Faraday Trans. 1996, 92, 293.
13. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
14. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
15. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
16. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
17. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
18. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
19. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
20. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
21. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
22. For recent reports of aerobic alcohol oxidation, see: (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (d) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (e) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (f) Dijksman, A.; Marino-Gonzalez, A.; Payeras, A. M. I.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826. (g) Son, Y.-C.; Makwana, V. D.; Howell, A. R.; Suib, S. L. Angew. Chem., Int. Ed. 2001, 40, 4280. (h) Liotta, L. F.; Venezia, A. M; Deganello, G.; Longo, A.; Martorana, A.; Schay, Z.; Guczi, L. Catal. Today 2001, 66, 271. (i) Döbler, C.; Mehtretter, G. M.; Sundermeier, U.; Eckert, M.; Militzer, H.-C.; Beller, M. Tetrahedron Lett. 2001, 42, 8447. (j) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
23. See Supporting Information for experimental details.
24. For recent reports of heterogeneous Pd-catalyzed Heck and Suzuki reactions, see: (a) Christian, P. M.; David, W. W.; Jackie, Y. Y. J. Am. Chem. Soc. 1998, 120, 12289. (b) Jayasree, S.; Seayad, A.; Laurent, R. D.; Henrike, H.; Klaus, K. J. Am. Chem. Soc. 2001, 123, 5990. (c) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 23. (d) Köhler, K.; Heidenreich, R. G.; Krauter, J.-G. E.; Pietsch, J. Chem.-Eur. J. 2002, 8, 622.
25. For recent reports of heterogeneous Pd-catalyzed Heck and Suzuki reactions, see: (a) Christian, P. M.; David, W. W.; Jackie, Y. Y. J. Am. Chem. Soc. 1998, 120, 12289. (b) Jayasree, S.; Seayad, A.; Laurent, R. D.; Henrike, H.; Klaus, K. J. Am. Chem. Soc. 2001, 123, 5990. (c) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 23. (d) Köhler, K.; Heidenreich, R. G.; Krauter, J.-G. E.; Pietsch, J. Chem.-Eur. J. 2002, 8, 622.
26. For recent reports of heterogeneous Pd-catalyzed Heck and Suzuki reactions, see: (a) Christian, P. M.; David, W. W.; Jackie, Y. Y. J. Am. Chem. Soc. 1998, 120, 12289. (b) Jayasree, S.; Seayad, A.; Laurent, R. D.; Henrike, H.; Klaus, K. J. Am. Chem. Soc. 2001, 123, 5990. (c) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 23. (d) Köhler, K.; Heidenreich, R. G.; Krauter, J.-G. E.; Pietsch, J. Chem.-Eur. J. 2002, 8, 622.
27. For recent reports of heterogeneous Pd-catalyzed Heck and Suzuki reactions, see: (a) Christian, P. M.; David, W. W.; Jackie, Y. Y. J. Am. Chem. Soc. 1998, 120, 12289. (b) Jayasree, S.; Seayad, A.; Laurent, R. D.; Henrike, H.; Klaus, K. J. Am. Chem. Soc. 2001, 123, 5990. (c) Mubofu, E. B.; Clark, J. H.; Macquarrie, D. J. Green Chem. 2001, 3, 23. (d) Köhler, K.; Heidenreich, R. G.; Krauter, J.-G. E.; Pietsch, J. Chem.-Eur. J. 2002, 8, 622.
28. There is controversy whether the Heck reaction using solid Pd catalysts occurred on their surface or not, see: (a) Zhao, F.; Murakami, K.; Shirai, M.; Arai, M. J. Catal. 2000, 194, 479. (b) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
29. There is controversy whether the Heck reaction using solid Pd catalysts occurred on their surface or not, see: (a) Zhao, F.; Murakami, K.; Shirai, M.; Arai, M. J. Catal. 2000, 194, 479. (b) Davies, I. W.; Matty, L.; Hughes, D. L.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 10139.
30. Fauvarque, J.-F.; Pflüger, F. J. Organomet. Chem. 1981, 208, 419.
31. Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
32. (a) Herrmann, W. A.; Brossmer. C.; Öfele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844.
33. (b) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.