Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction

Advanced Synthesis and Catalysis

Volumn 347, Issue 5, 2005, Pages 647-654

  Andrews, Stephen P ^a   Stepan, Antonia F ^a   Tanaka, Hirohisa ^b   Ley, Steven V ^a   Smith, Martin D ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b DAIHATSU MOTOR CO LTD   (Japan)

Author keywords

Cross coupling; Heterogeneous catalysis; Homogeneous catalysis; Palladium; Perovskite; Suzuki reaction

Indexed keywords

PALLADIUM; PALLADIUM COMPLEX; PEROVSKITE;

ARTICLE; CATALYST; KINETICS; MICROSCOPY; SUZUKI REACTION;

EID: 18244366860     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404331     Document Type: Article

References (47)

1. The classical, solubility-based definition equates " heterogeneous" to "insoluble" and "homogeneous" to "soluble". When referring to this definition, quotation marks will be used ('homogeneous', 'heterogeneous'). A newer definition deals with the active site of the catalytic system: see J. Schwartz, Acc. Chem. Res. 1985, 18, 302. If the active site is uniform, the system is called homogeneous; if the active site consists of irregular sites, then the catalyst is called heterogeneous. When referring to this definition no quotation marks will be used.
2. R. B. Bedford, S. L. Hazelwood, M. E. Limmert, Chem. Commun. 2002, 2610.
3. R. B. Bedford, S. L. Welch, Chem. Commun. 2001, 129.
4. J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550.
5. S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. Int. Edit. 2004, 43, 1871.
6. A. F. Littke, G. C. Fu, Angew. Chem. Int. Edit. 2002, 41, 4176.
7. A. F. Littke, C. Y. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020.
8. C. E. Garrett, K. Prasad, Adv. Synth. Catal. 2004, 346, 889.
9. C. Ramarao, S. V. Ley, S. C. Smith, I. M. Shirley, N. DeAlmeida, Chem. Commun. 2002, 1132.
10. S. V. Ley, C. Mitchell, D. Pears, C. Ramarao, J. Q. Yu, W. Z. Zhou, Org. Lett. 2003, 5, 4665.
11. S. Kobayashi, R. Akiyama, Chem. Commun. 2003, 449.
12. R. Akiyama, S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3412.
13. K. Okamoto, R. Akiyama, S. Kobayashi, Org. Lett. 2004, 6, 1987.
14. B. M. Trost, E. Keinan, J. Am. Chem. Soc. 1978, 100, 7779.
15. A. Datta, K. Ebert, H. Plenio, Organometallics 2003, 22, 4685.
16. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, J. Org. Chem. 2003, 68, 7733.
17. K. Köhler, R. G. Heidenreich, J. G. E. Krauter, M. Pietsch, Chem. Eur. J. 2002, 8, 622.
18. R. G. Heidenreich, E. G. E. Krauter, J. Pietsch, K. Köhler, J. Mol. Catal. A: Chem. 2002, 182, 499.
19. R. G. Heidenreich, K. Köhler, J. G. E. Krauter, J. Pietsch, Synlett 2002, 1118.
20. Z. Novak, A. Szabo, J. Repasi, A. Kotschy, J. Org. Chem. 2003, 68, 3327.
21. N. E. Leadbeater, M. Marco, Angew. Chem. Int. Edit. 2003, 42, 1407.
22. N. E. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 5660.
23. S. S. Prockl, W. Kleist, M. A. Gruber, K. Köhler, Angew. Chem. Int. Edit. 2004, 43, 1881.
24. D. A. Conlon, B. Pipik, S. Ferdinand, C. R. LeBlond, J. R. Sowa, B. Izzo, P. Collins, G. J. Ho, J. M. Williams, Y. J. Shi, Y. K. Sun, Adv. Synth. Catal. 2003, 345, 931.
25. I. W. Davies, L. Matty, D. L. Hughes, P. J. Reider, J. Am. Chem. Soc. 2001, 123, 10139.
26. A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem. 2001, 1131.
27. Y. Na, S. Park, S. B. Han, H. Han, S. Ko, S. Chang, J. Am. Chem. Soc. 2004, 126, 250.
28. C. A. Jaska, I. Manners, J. Am. Chem. Soc. 2004, 126, 9776.
29. Y. Nishihata, J. Mizuki, T. Akao, H. Tanaka, M. Uenishi, M. Kimura, T. Okamoto, N. Hamada, Nature 2002, 418, 164.
30. N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513.
31. M. D. Smith, A. F. Stepan, C. Ramarao, P. E. Brennan, S. V. Ley, Chem. Commun. 2003, 2652.
32. This is an improvement on our previously disclosed value of 27,000.
33. F. G. J. Rebek, S. Zimmerman, J. Am. Chem. Soc. 1975, 97, 454.
34. F. G. J. Rebek, J. Am. Chem. Soc. 1974, 96, 7112.
35. J. A. Widegren, M. A. Bennett, R. G. Finke, J. Am. Chem. Soc. 2003, 125, 10301.
36. J. A. Widegren, R. G. Finke, J. Mol. Catal. A: Chem. 2003, 198, 317.
37. B. H. Lipshutz, S. Tasler, W. Chrisman, B. Spliethoff, B. Tesche, J. Org. Chem. 2003, 68, 1177.
38. P. M. Maitlis, J. Mol. Cat. 1980, 7, 543.
39. M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 14, 1559.
40. M. T. Reetz, E. Westermann, Angew. Chem. Int. Edit. 2000, 39, 165.
41. B. J. Hornstein, J. D. Aiken, R. G. Finke, Inorg. Chem. 2002, 41, 1625.
42. In cases where a heterogeneous precatalyst generates a catalytically active soluble catalyst, the stoichiometry of such poisoning studies are useful for the calculation of turnover numbers but are not particularly informative for the investigation of homogeneous versus heterogeneous mechanisms.
43. 2 required to stop any catalysis.
44. C. Amatore, A. Jutand, Acc. Chem. Res. 2000, 33, 314.
45. D. Zim, A. L. Monteiro, J. Dupont. Tetrahedron Lett. 2000, 41, 8199.
46. A. H. M. de Vries, J. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
47. Y. J. Deng, L. Z. Gong, A. Q. Mi, H. Liu, Y. Z. Jiang, Synthesis 2003, 337.