Palladium-catalyzed multiple aryl animations of polybromobenzenes

Synlett

Volumn , Issue 5, 1998, Pages 504-506

  Witulski, Bernhard ^a   Senft, Stefan ^a   Thum, Andreas ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001769633     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1692     Document Type: Article

References (44)

1. Wolff, J. J.; Zietsch, A.; Irngartinger, H.; Oeser, T. Angew. Chem. 1997, 109, 637;
2. Angew. Chem. Int. Ed. Engl. 1997, 36, 621.
3. Effenberger, F.; Mündel, G. Chem. Ber. 1992, 125, 247.
4. Upsani, R. B.; Chiang, L. Y.; Goshorn, D. P.; Tindall, P. Mol. Cryst. Liq. Cryst. 1990, 190, 35.
5. Dietrich, M.; Heinze, J. J. Am. Chem. Soc. 1990, 112, 5142.
6. Chance, J. M.; Kahr, B.; Buda, A. B.; Toscano, J. P.; Mislow, K. J. Org. Chem. 1988, 53, 3226.
7. Elbl, K.; Krieger, C.; Staab, H. A. Angew. Chem. 1986, 98, 1024;
8. Angew. Chem. Int. Ed. Engl. 1986, 25, 1023.
9. Keller, H. J.; Niebl, R.; Renner, G.; von der Ruhr, D.; Kilic, A. K.; Schweitzer, D. Z. Naturforsch. 1989, 44b, 327.
10. Effenberger, F. Acc. Chem. Res. 1989, 22, 27.
11. Stickley, K. R.; Blackstock, S. C. J. Am. Chem. Soc. 1994, 116, 11576.
12. Krusic, P. J.; Wasserman, E. J. Am. Chem. Soc. 1991, 113, 2322.
13. Miller, J. S.; Dixon, D. A.; Calabrese, J. C.; Vazquez, C.; Krusic, P. J.; Ward, M. D.; Wasserman, E.; Harlow, R. L. J. Am. Chem. Soc. 1990, 112, 381.
14. Thomaides, J.; Maslak, P.; Breslow, R. J. Am. Chem. Soc. 1988, 110, 3970.
15. Effenberger, F.; Prossel, G.; Auer, E.; Fischer, P. Chem. Ber. 1970, 103, 1456.
16. Effenberger, F.; Auer, E.; Fischer, P. Chem. Ber. 1970, 103, 1440.
17. Effenberger, F.; Niess, R. Chem. Ber. 1968, 101, 3787.
18. Biemans, H. A. M.; Zhang, C.; Smith, P.; Kooijman, H.; Smeets, W. J. J.; Spek, A. L.; Meijer, E. W. J. Org. Chem. 1996, 61, 9012.
19. Wolff, J. J.; Limbach, H.-H. Liebigs Ann. Chem. 1991, 691.
20. Praefcke, K.; Kohne, B.; Korinth, F.; Psaras, P.; Nasielski, J.; Verhoeven, C.; Nasielski-Hinkens, R. Liebigs Ann. Chem. 1989, 617.
21. Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451.
22. Hartwig, J. F. Synlett 1997, 329.
23. Marcoux, J. F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
24. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
25. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
26. Guram, S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. 1995, 107, 1456;
27. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.
28. For Pd-catalyzed polycondensations between 1,3-bisanilines and 6 see: Kanbara, T.; Izumi, K.; Nakadani, Y.; Narise, T.; Hasegawa, K. Chem. Lett. 1997, 1185.
29. Diercks, R.; Armstrong, J. C.; Boese, R.; Vollhardt, K. P. C. Angew. Chem. 1986, 98, 270;
30. Angew. Chem. Int. Ed. Engl. 1986, 25, 268.
31. Boese, R.; Green, J. R.; Mittendorf, J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem. 1992, 104, 1643;
32. Angew. Chem. Int. Ed. Engl. 1992, 31, 1643.
33. Rinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem. 1997, 109, 1343;
34. Angew. Chem. Int. Ed. Engl. 1997, 36, 1289.
35. Synthesis of 1,2,3-tri-bromobenzene 17: Tietze, L. F.; Eicher, Th. Reaktionen und Synthesen Thieme: Stuttgart, 1991, p. 501.
36. The morpholinobenzenes 7, 10, 12, 14, and 16 have been previously synthesized by non-catalytic methods: 7 and 12: Kawaguchi, M.; Ohashi, J. Synthesis 1985, 701.
37. 10: Axe, W. N.; Freeman, C. J. Am. Chem. Soc. 1934, 56, 478.
38. 14: Effenberger, F.; Niess, R. Angew. Chem. 1967, 79, 1100;
39. Angew. Chem. Int. Ed. Engl. 1967, 6, 1067.
40. 16: Baroni, S.; Rivera, E.; Stradi, R.; Sacarello, M. L. Tetrahedron Lett. 1980, 21, 889.
41. 13C NMR, elemental analysis and/or HRMS.
42. For recent investigations to utilize 18 in the synthesis of discrete molecular weight dendrimers via the aryl amination protocol see: Louie, J.; Hartwig, J. F.; Fry, A. J. J. Am. Chem. Soc. 1997, 119, 11695.
43. 6 558.3471; found 558.3486.
44. 3 calc.: C 64.84, H 8.16, N 12.60; found: C 64.79, H 8.11, N 12.77.