Recent developments in palladium-catalyzed coupling reactions

Letters in Organic Chemistry

Volumn 2, Issue 2, 2005, Pages 113-117

  van de Weghe, Pierre ^a  

^a Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

Negishi reactions; Oxidative addition; Phosphaadamantanes; Phosphines; Suzuki miyaura crosscoupling; Transmetallation

Indexed keywords

EID: 29744461509     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570178053202991     Document Type: Review

References (36)

1. (a) Top. Curr. Chem.; Miyaura, N., Ed.; Springer-Verlag: Berlin-Heidelberg, 2002; Vol. 219.
2. (b) Tsuji, J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis, Wiley: New-York, 1995.
3. (c) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 2419.
4. Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
5. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
6. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2001, 40, 4544.
7. (c) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
8. (d) Cárdenas, D. J. Angew. Chem. Int. Ed. 2003, 42, 384.
9. (e) Miura, M. Angew. Chem. Int. Ed. 2004, 43, 2201.
10. Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691.
11. (a) Netherton, M. R.; Chaoyang, D.; Neuschütz, K.; Fu, G, C. J. Am. Chem. Soc. 2001, 123, 10099.
12. (b) A nickel/bathophenanthroline based system catalyst has been found to be a very efficient in cross-coupling of unactivated secondary alkyl bromides and iodides with aryl boronic acids: Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
13. (a) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1945.
14. (b) Netherton,M. R.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 3910.
15. (c) Brenstrum, T.; Gerristma, D. A.; Adjabeng, G. M.; Frampton, C. S.; Britten, J.; Robertson, A. J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 7635.
16. (d) Adjabeng, G.; Brenstrum, T.: Frampton. C. S.: Robertson. A. J.: Hillhouse, J.; McNulty, J.; Capretta, A. J. Org. Chem. 2004, 69, 5082.
17. (a) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1998, 37, 3387.
18. (b) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
19. (a) Wolfe, J. P.; Singer, R.A.; Yang, B.H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
20. (b) Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.
21. Waker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem. Int. Ed. 2004, 43, 1871.
22. Kwong, F. Y.; Lam, W. H.; Yeung, C. H.; Chan, K. S.; Chan, A. S. C. Chem. Commun. 2004, 1922.
23. (a) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
24. (b) Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
25. (a) Alcazar-Roman, L. M.; Hartwing, J. F. J. Am. Chem. Soc. 2001, 123, 12905.
26. (b) Strieter, E. R.; Blackmond, D. G.; BuchwLdd, S. L. J. Am. Chem. Soc. 2003, 125, 13978.
27. (c) Stambuli, J. P.; Incarvito, C. D.; Bühl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 1184.
28. (a) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
29. (b) For the recent cross-coupling of unactivated secondary alkyl halides catalyzed by a nickel/Pybox system, see: Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726.
30. (c) Wiskur, S. L.; Korte, A.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 82.
31. (a) Hundertmark, T.; Littke, A. F.; Buchwald, S. F.; Fu, G. C. Org. Lett. 2000, 2, 1729.
32. 2 were recently used in sterically hindered substrates at room temperature in Suzuki-Miyaura cross-coupling: Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195.
33. Urgaonkar, S.; Verkade, J. G. J. Org. Chem. 2004, 69, 5752.
34. Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
35. (a) Moreno-Mañas, M.; Pleixats, R. Acc. Chem. Res. 2003, 36, 638.
36. (b) Reetz, M. T.; de Vries, J. G. Chem. Commun. 2004, 1559.