Highly Active Thermomorphic Fluorous Palladacycle Catalyst Precursors for the Heck Reaction; Evidence for a Palladium Nanoparticle Pathway

Organic Letters

Volumn 4, Issue 12, 2002, Pages 1993-1996

  Rocaboy, Christian ^a   Gladysz, J A ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0001489150     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025790r     Document Type: Article

References (48)

1. (a) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
2. (b) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37.
3. (c) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183.
4. (d) Hope, E. G.; Stuart, A. M. J. Fluorine Chem. 1999, 100, 75.
5. Survey of practical considerations and underlying physical principles: Barthel-Rosa, L. P.; Gladysz, J. A. Coord. Chem. Rev. 1999, 190-192, 587.
6. (a) Horváth, I. T.; Kiss, G.; Cook, R. A.; Bond, J. E.; Stevens, P. A.; Rábai, J.; Mozeleski, E. J. J. Am. Chem. Soc. 1998, 120, 3133.
7. (b) Foster, D. F.; Gudmunsen, D.; Adams, D. J.; Stuart, A. M.; Hope, E. G.; Cole-Hamilton, D. J.; Schwarz, G. P.; Pogorzelec, P. Tetrahedron 2002, 58, in press.
8. (a) Rutherford, D.; Juliette, J. J. J.; Rocaboy, C.; Horváth, I. T.; Gladysz, J. A. Catal. Today 1998, 42, 381.
9. (b) Richter, B.; Spek, A. L.; van Koten, G.; Deelman, B.-J. J. Am. Chem. Soc. 2000, 122, 3945.
10. Juliette, J. J. J.; Rutherford, D.; Horváth, I. T.; Gladysz, J. A. J. Am. Chem. Soc. 1999, 121, 2696.
11. (a) Dinh, L. V.; Gladysz, J. A. Tetrahedron Lett. 1999, 40, 8995.
12. (b) de Wolf, E.; Speets, E. A.; Deelman, B.-J.; van Koten, G. Organometallics 2001, 20, 3686.
13. (a) Quici, S.; Cavazzini, M.; Ceragioli, S.; Montanari, F.; Pozzi, G. Tetrahedron Lett. 1999, 40, 3647.
14. (b) Pozzi, G.; Cavazzini, M.; Cinato, F.; Montanari, F.; Quici, S. Eur. J. Org. Chem. 1999, 1947.
15. (c) Nishimura, T.; Maeda, Y.; Kakiuchi, N.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 2000, 4301.
16. (d) Colonna, S.; Gaggero, N.; Montanari, F.; Pozzi, G.; Quici, S. Eur. J. Org. Chem. 2001, 181.
17. (e) Ragagnin, G.; Betzmeier, B.; Quici, S.; Knochel, P. Tetrahedron 2002, 58, 3985.
18. Moineau, J.; Pozzi, G.; Quici, S.; Sinou, D. Tetrahedron Lett. 1999, 40, 7683.
19. Reviews: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (b) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
20. Reviews: (a) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. (b) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
21. Other carbon-carbon bond forming reactions catalyzed by fluorous palladium precursors: (a) Schneider, S.; Bannwarth, W. Angew. Chem., Int. Ed. 2000, 39, 4142; Angew. Chem. 2000, 112, 4293.
22. Other carbon-carbon bond forming reactions catalyzed by fluorous palladium precursors: (a) Schneider, S.; Bannwarth, W. Angew. Chem., Int. Ed. 2000, 39, 4142; Angew. Chem. 2000, 112, 4293.
23. (b) Schneider, S.; Bannwarth, W. Helv. Chim. Acta 2001, 84, 735.
24. (c) Saito, S.; Chounan, Y.; Nogami, T.; Ohmori, O.; Yamamoto, Y. Chem. Lett. 2001, 444.
25. (d) Rocaboy, C.; Gladysz, J. A. Tetrahedron 2002, 58, 4007.
26. (a) Rocaboy, C.; Rutherford, D.; Bennett, B. L.; Gladysz, J. A. J. Phys. Org. Chem. 2000, 13, 596.
27. (b) Rocaboy, C.; Hampel, F.; Gladysz, J. A. J. Org. Chem. 2002, 67, in press.
28. Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490.
29. (a) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357.
30. (b) Closely related catalyst precursors with additional phenyl rings: Blackmond, D. G.; Rosner, T.; Pfaltz, A. Org. Proc. Res. Dev. 1999, 3, 275.
31. (c) Additional catalyst precursors with nitrogen-donor palladacycles: Beletskaya, I. P.; Kashin, A. N.; Karlstedt, N. B.; Mitin, A. V.; Cheprakov, A. V.; Kazankov, G. M. J. Organomet. Chem. 2001, 622, 89.
32. Soós, T.; Bennett, B. L.; Rutherford, D.; Barthel-Rosa, L. P.; Gladysz, J. A. Organometallics 2001, 20, 3079.
33. Rocaboy, C.; Bauer, W.; Gladysz, J. A. Eur. J. Org. Chem. 2000, 2621.
34. 5 were much higher above 50°C, allowing NMR spectra to be recorded.
35. Note that regardless of identity of the active catalyst, the iodide ions liberated during the Heck coupling should convert remaining 2 to 3.
36. Gladysz, J. A. Pure Appl. Chem. 2001, 73, 1319.
37. (a) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165; Angew. Chem. 2000, 112, 170 and earlier papers referenced therein.
38. (a) Reetz, M. T.; Westermann, E. Angew. Chem., Int. Ed. 2000, 39, 165; Angew. Chem. 2000, 112, 170 and earlier papers referenced therein.
39. (b) Le Bars, J.; Specht, U.; Bradley, J. S.; Blackmond, D. G. Langmuir 1999, 15, 7621.
40. (a) Yeung, L. K.; Crooks, R. M. Nano Lett. 2001, 1, 14.
41. (b) Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181 and additional references therein.
42. (a) Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Organometallics 2001, 20, 4524.
43. (b) See also: Moreno-Mañas, M.; Pleixats, R.; Villarroya, S. Chem. Commun. 2002, 60.
44. Nowotny, M.; Hanefeld, U.; van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877.
45. (a) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
46. (b) Zhao, F.; Bhanage, B. M.; Shirai, M.; Arai, M. Chem. Eur. J. 2000, 6, 843.
47. (a) Rosner, T.; Le Bars, J.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 1848.
48. (b) Rosner, T.; Pfaltz, A.; Blackmond, D. G. J. Am. Chem. Soc. 2001, 123, 4621.