Palladium versus copper-catalyzed N-arylation towards an efficient access to polysubstituted dibenzophenanthrolines and carbazoles

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2589-2592

  Jacquelin, Clémence ^a   Saettel, Nicolas ^a   Hounsou, Candide ^a   Teulade Fichou, Marie Paule ^a  

^a l'alimentation et l'Environnement   (France)

Author keywords

Functional carbazoles; N Arylation; Palladium and copper catalysis; Polysubstituted dibenzo phenanthrolines; Selective arylation

Indexed keywords

ALDEHYDE; ANTHRANILIC ACID DERIVATIVE; BENZENE DERIVATIVE; CARBAZOLE DERIVATIVE; COPPER; DIAMINE; PALLADIUM; PHENANTHROLINE DERIVATIVE;

AMINATION; ARTICLE; ARYLATION; CATALYSIS;

EID: 15244344518     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.079     Document Type: Article

References (44)

1. For a review see: M. Demeunynck C. Bailly W.D. Wilson DNA and RNA binders: from Small Molecules to Drugs Vols. 1 and 2 2003 Wiley-VCH
2. G. Parkinson, and S. Neidle Nature Rev., Drug Discovery 2002 383 393
3. M. Magoga, and C. Joachim Phys. Rev. B 56 1997 4722 4729
4. J. Qu, D. Liu, S. De Feyter, J. Zhang, F.C. De Schryver, and K. Müllen J. Org. Chem. 63 1999 9802 9808
5. R. De Bettignies, Y. Nicolas, P. Blanchard, E. Levillain, J.-M. Nunzi, and J. Roncali Adv. Mater. 15 2003 1940 1943
6. F. Würthner Angew. Chem., Int. Ed. 40 2001 1037 1039
7. E.C. Riesgo, X. Jin, and R.P. Thummel J. Org. Chem. 61 1996 3017 3022
8. S. Gladiali, G. Chelucci, M.S. Mudadu, M.-A. Gastaut, and R.P. Thummel J. Org. Chem. 66 2001 400 405
9. T.W. Bell, A.B. Khasanov, M.G.B. Drew, A. Filikov, and T.L. James Angew. Chem., Int. Ed. 38 1999 2543 2547
10. C.-S. Choi, T. Mutai, S. Arita, and K. Araki J. Chem. Soc., Perkin Trans. 2 2000 243 247
11. G. Kaupp, and M.R. Naimi-Jamal Eur. J. Org. Chem. 2002 1368 1373
12. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400 5449
13. C. Couture, and A.J. Paine Can. J. Chem. 63 1985 111 120
14. J.F. Hartwig Angew. Chem., Int. Ed. 37 1998 2046 2067
15. A.R. Muci, and S.L. Buchwald Top. Curr. Chem. 219 2002 131 209
16. D. Prim, J.-M. Campagne, D. Joseph, and B. Andrioletti Tetrahedron 58 2002 2041 2075
17. J.C. Antilla, J.M. Baskin, T.E. Barder, and S.L. Buchwald J. Org. Chem. 69 2004 5578 5587
18. C. Enguehard, H. Allouchi, A. Gueiffer, and S.L. Buchwald J. Org. Chem. 68 2004 4367 4370
19. H.-J. Cristau, P.C. Cellier, J.-F. Spindler, and M. Taillefer Chem. Eur. J. 10 2004 5607 5622
20. H.-J. Cristau, P.C. Cellier, J.-F. Spindler, and M. Taillefer Org. Lett. 6 2004 913 916
21. F.Y. Kwong, A. Klapars, and S.L. Buchwald Org. Lett. 4 2002 581 584
22. O. Baudoin, M.-P. Teulade-Fichou, J.-P. Vigneron, and J.-M. Lehn J. Org. Chem. 16 1997 5458 5470
23. O. Baudoin, C. Marchand, M.-P. Teulade-Fichou, J.-P. Vigneron, J.-S. Sun, T. Garestier, C. Hélène, and J.-M. Lehn Chem. Eur. J. 4 1998 1504 1508
24. J.-L. Mergny, L. Lacroix, M.-P. Teulade-Fichou, C. Hounsou, L. Guittat, M. Hoarau, P.B. Arimondo, J.-P. Vigneron, J.-M. Lehn, J.-F. Riou, T. Garestier, and C. Hélène Proc. Natl. Acad. Sci. U.S.A. 98 2001 3062 3067
25. M.-P. Teulade-Fichou, J.-P. Vigneron, and J.-M. Lehn J. Supramol. Chem. 5 1995 139 145
26. A.J. Paine J. Am. Chem. Soc. 109 1987 1496 1502
27. H.B. Goodbrand, and N.-X. Hu J. Org. Chem. 64 1999 670 674
28. A. Kiyomori, J.-F. Marcoux, and S.L. Buchwald Tetrahedron Lett. 40 1999 2657 2660
29. R.K. Gujadhur, C.G. Bates, and D. Venkataraman Org. Lett. 3 2001 4315 4317
30. R. Gujadhur, D. Venkataraman, and J.T. Kintigh Tetrahedron Lett. 42 2001 4791 4793
31. H. Liebermann Liebigs Ann. Chem. 518 1935 245 252
32. J.-F. Constant, J. Fahy, and J. Lhomme Tetrahedron Lett. 28 1987 1177 1179
33. R.F. Pellon, R. Carrasco, and L. Rodes Synth. Commun. 26 1996 3869 3876
34. A.A. Kelkar, N.M. Patil, and R.V. Chaudhari Tetrahedron Lett. 43 2002 7143 7146
35. J.P. Wolfe, and S.L. Buchwald Tetrahedron Lett. 38 1997 6359 6362
36. X. Huang, K.W. Anderson, D. Zim, L. Jiang, A. Klapars, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 6653 6655
37. 12a
38. I.P. Beletskaya, A.G. Bessmertnykh, and R. Guilard Synlett 1999 1459 1461
39. J.F. Hartwig, S. Richards, D. Baranano, and F. Paul J. Am. Chem. Soc. 118 1996 3626 3633
40. D.E. Ames, and A. Opalko Tetrahedron 40 1984 1919 1925
41. I.C.F.R. Ferreiera, M.-J.R.P. Queiroz, and G. Kirsch Tetrahedron 59 2003 3737 3743
42. R.B. Bedford, and C.S.J. Cazin Chem. Commun. 2002 2310 2311
43. H.J. Knölker, and R.K. Reddy Chem. Rev. 102 2002 4303 4427
44. T. Wenderski, K.M. Light, D. Ogrin, S.G. Bott, and C.J. Harlan Tetrahedron Lett. 43 2004 6851 6853