Palladium nanoclusters in Sonogashira cross-coupling: A true catalytic species?

Advanced Synthesis and Catalysis

Volumn 347, Issue 15, 2005, Pages 1965-1968

  Thathagar, Mehul B ^a   Kooyman, Patricia J ^b   Boerleider, Romilda ^a   Jansen, Eveline ^a   Elsevier, Cornelis J ^a   Rothenberg, Gadi ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DelftChemTech   (Netherlands)

Author keywords

Aryl halides; Catalysis; Kinetics; Leaching; Palladium; TEM

Indexed keywords

EID: 29144522294     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505229     Document Type: Article

References (47)

1. For a general overview on metal nanoclusters and their applications in catalysis, see: a) J. D. Aiken III, R. G. Finke, J. Mol. Catal. A 1999, 145, 1;
2. b) J. S. Bradley, E. Hill, M. E. Leonowicz, H. Witzke, J. Mol. Catal. 1987, 41, 59;
3. c) H. Bönnemann, R. M. Richards, Eur. J. Org. Chem. 2001, 2455.
4. a) M. Moreno-Mañas, R. Pleixats, Acc. Chem. Res. 2003, 36, 638;
5. b) M. B. Thathagar, J. Beckers, G. Rothenberg, J. Am. Chem. Soc. 2002, 124, 11858;
6. c) M. B. Thathagar, J. Beckers, G. Rothenberg, Adv. Synth. Catal. 2003, 345, 979;
7. d) M. Beller, H. Fischer, K. Kuhlein, C. P. Reisinger, W. A. Herrmann, J. Organomet. Chem. 1996, 520, 257.
8. a) F. Y. Zhao, B. M. Bhanage, M. Shirai, M. Arai, Chem. Eur. J. 2000, 6, 843;
9. b) R. L. Augustine, S. T. Oleary, J. Mol. Catal. A 1995, 95, 277;
10. c) A. Biffis, M. Zecca, M. Basato, J. Mol. Catal. A 2001, 173, 249;
11. d) B. M. Choudary, S. Madhi, N. S. Chowdari, M. L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2002, 124, 14127;
12. e) S. S. Prockl, W. Kleist, M. A. Gruber, K. Köhler, Angew. Chem. Int. Ed. 2004, 43, 1881;
13. f) K. Köhler, R. G. Heidenreich, J. G. E. Krauter, M. Pietsch, Chem. Eur. J. 2002, 8, 622.
14. 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.
15. C. C. Cassol, A. P. Umpierre, G. Machado, S. I. Wolke, J. Dupont, J. Am. Chem. Soc. 2005, 127, 3298.
16. M. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165.
17. J. Hu, Y. B. Liu, Langmuir 2005, 21, 2121.
18. J. A. Hamlin, K. Hirai, A. Millan, P. M. Maitlis, J. Mol. Catal. 1980, 7, 543.
19. J. A. Widegren, R. G. Finke, J. Mol. Catal. A: Chem. 2003, 198, 317.
20. Y. Li, E. Boone, M. A. El-Sayed, Langmuir 2002, 18, 4921.
21. J. Le Bars, U. Specht, J. S. Bradley, D. G. Blackmond, Langmuir 1999, 15, 7621.
22. M. B. Thathagar, J. Beckers, G. Rothenberg, Green Chem. 2004, 6, 215.
23. a) R. W. J. Scott, O. M. Wilson, R. M. Crooks, J. Phys. Chem. B 2005, 109, 692;
24. b) S. U. Son, Y. Jang, J. Park, H. B. Na, H. M. Park, H. J. Yun, J. Lee, T. Hyeon, J. Am. Chem. Soc. 2004, 126, 5026;
25. c) K. Nagaveni, A. Gayen, G. N. Subbanna, M. S. Hegde, J. Mater. Chem. 2002, 12, 3147;
26. d) J. Park, E. Kang, S. U. Son, H. M. Park, M. K. Lee, J. Kim, K. W. Kim, H. J. Noh, J. H. Park, C. J. Bae, J. G. Park, T. Hyeon, Adv. Mater. 2005, 17, 429;
27. e) H. G. Lang, S. Maldonado, K. J. Stevenson, B. D. Chandler, J. Am. Chem. Soc. 2004, 126, 12949.
28. K. Sonogashira, in: Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1997, p. 203.
29. A. Biffis, M. Zecca, M. Basato, J. Mol. Catal. A 2001, 173, 249.
30. The Heck reaction is often used as an example in mechanistic studies on cross-coupling, but the problem is that the high temperatures can affect the surface chemistry of the Pd clusters and influence the leaching of Pd atoms.
31. J. S. Bradley, B. Tesche, W. Busser, M. Maase, M. T. Reetz, J. Am. Chem. Soc. 2000, 122, 4631.
32. R. Narayanan, M. A. El-Sayed, J. Am. Chem. Soc. 2003, 125, 8340.
33. A. Howard, C. E. J. Mitchell, R. G. Egdell, Surf. Sci. 2002, 515, L504.
34. A. H. M. de Vries, J. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
35. A. Biffis, M. Zecca, M. Basato, Eur. J. Inorg. Chem. 2001, 1131.
36. A. H. M. de Vries, F. J. Parlevliet, L. Schmieder-van de Vondervoort, J. H. M. Mommers, H. J. W. Henderickx, M. A. M. Walet, J. G. de Vries, Adv. Synth. Catal. 2002, 344, 996.
37. M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559.
38. 3 instead of TBAA yielded larger particles as well as Pd black. See supporting information for details.
39. The above deductions are based on initial rate studies. In principle, it should be possible to fit a more detailed model to the entire kinetic curve, provided one has sufficient data points to carry out a residuals analysis. This can be done, for example, using time-resolved in situ spectroscopy. However, the Sonogashira reaction profiles were obtained using GC analysis and were not sufficiently detailed for residuals analysis. For a discussion on the application of such methods to Heck cross-coupling, see: G. Rothenberg, S. C. Cruz, G. P. F. Van Strijdonck, H. C. J. Hoefsloot, Adv. Synth. Catal. 2004, 346, 467.
40. R. G. Finke, S. Özkar, Coord. Chem. Rev. 2004, 248, 135.
41. S. Özkar, R. G. Finke, J. Am. Chem. Soc. 2002, 124, 5796.
42. M. Maekawa, M. Munakata, T. Kuroda-Sowa, Y. Suenaga, Anal. Sci. 1998, 14, 447.
43. C. Amatore, E. Carre, A. Jutand, M. A. Mbarki, G. Meyer, Organometallics 1995, 14, 5605.
44. D. Méry, K. Héuze, D. Astruc, Chem. Commun. 2003, 1934.
45. X. Fu, S. Zhang, J. Yin, D. P. Schumacher, Tetrahedron Lett. 2002, 43, 6673.
46. D. A. Alonso, C. Nájera, M. C. Pacheco, Tetrahedron Lett. 2002, 43, 9365.
47. C. Amatore, S. Bensalem, S. Ghalem, A. Jutand, Y. Medjour, Eur. J. Org. Chem. 2004, 366.