Palladium-catalyzed synthesis of aryl-substituted polyamine compounds from aryl halides

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2287-2290

  Beletskaya, Irina P ^a   Bessmertnykh, Alla G ^a   Guilard, Roger ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

POLYAMINE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592580     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00363-8     Document Type: Article

References (25)

1. 1. Cramer, R.; Coulson, D. R. J. Org. Chem, 1975, 40, 2267-2273,
2. (b) Progress in polyamine research. Novel Biochemical, Pharmacological, and Clinical Aspects; Zappia, V.; Pegg, A. E. Eds.; Plenum Press, Inc.: New York, 1989.
3. 2. (a) Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. Aza-Crown Macrocycles; Jon Wiley and Sons, Inc.: New York, 1993; Vol. 51.
4. (b) McWhinnie, S. L. W. Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem. 1993, 1993, 303-307.
5. (c) Togni, A.; Venanzi, L. M. Ang. Chem., Int. Ed. Eng. 1994, 33, 497-526.
6. 3. (a) March, J. Advanced Organic Chemistry; John Wiley and Sons, Inc.: New York, 1992.
7. (b) Heaney, H. Chem. Reviews 1962, 62, 81-97.
8. (c) Lindley, J. Tetrahedron 1984, 40, 1433-1456.
9. (d) Tsukube, H.; Minatogawa, H.; Munakata, M.; Toda, M.; Matsumoto, K. J. Org. Chem. 1992, 57, 542-547.
10. 4. (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902.
11. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Eng. 1995, 34, 1348-1350.
12. (c) Wolfe, J. P.; Buchwald, S. L. J. Org Chem. 1996, 61, 1133-1135.
13. (d) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
14. 5. (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Amer. Chem. Soc. 1994, 116, 5969-5970.
15. (b) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598-11599.
16. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
17. 6. (a) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
18. (b) Kosugi, M.; Kameyama, M.; Sano, H.; Migita, T. Nippon Kagaku Kaishi 1985, 3, 541-551.
19. 7. (a) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039.
20. (b) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794-2805.
21. 3. A slow reaction proceeds in the presence of NaOH.
22. 9. Sometimes the excess of dppf increased the rate of arylation (entry 3, Table 1; entry 1, Table 2; but not in the case of entry 4, Table 2).
23. 13C NMR spectroscopies, and MS spectrometry.
24. 11. Diaryl-substituted products (less than 15%) are observed only in entries 1,2 and 10, Table 1.
25. 2 with rather good yield was published, Zhao, S.-H.; Miller; A.K., Berger, J.; Flippin, L.A. Tetrahedron Lett. 1996, 37, 4463-4466.