Hartwig-Buchwald amination on solid supports: A novel access to a diverse set of 1H-benzotriazoles

Journal of Combinatorial Chemistry

Volumn 9, Issue 6, 2007, Pages 1114-1137

  Zimmermann, Viktor ^a   Bräse, Stefan ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; AMINE; ANILINE; ANILINE DERIVATIVE; BENZOTRIAZOLE; MACROCYCLIC COMPOUND; PALLADIUM; TRIAZENE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

ACIDS; AMINES; ANILINE COMPOUNDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; MACROCYCLIC COMPOUNDS; MODELS, CHEMICAL; PALLADIUM; STEREOISOMERISM; TEMPERATURE; TRIAZENES; TRIAZOLES;

EID: 36649034864     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc700105p     Document Type: Article

References (26)

1. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
2. (a) For an early example of Hartwig-Buchwald reactions on solid supports, see: Ketcha, D. M.; Wilson, L. J.; Portlock, D. E. Tetrahedron Lett. 2000, 41, 6253-6257.
3. (b) Further examples: Weigand, K.; Pelka, S. Org. Lett. 2002, 4, 4689-4692.
4. (c) Further examples: Weigand, K.; Pelka, S. Mol. Diversity 2003, 7, 181-184.
5. Lormann, M. E. P.; Walker, C. H.; Es-Sayed, M.; Bräse, S. Chem. Commun. 2002, 1296-1297.
6. Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V Chem. Rev. 1998, 98, 409-548.
7. A preliminary example has been presented in an account without any details: Bräse, S. Acc. Chem. Res. 2004, 37, 805-815.
8. Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories.
9. Dahmen, S.; Bräse, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Manko, R., Hartwig W., Eds.; VCH, Weinheim, 2002; Chapter 4.
10. The haloarenes, amines, and anilines used are commercially available from Aldrich. For 2b (giving rise to resin 4): Kleiderer, E. C.; Adams, R. J. Am. Chem. Soc. 1933, 55, 4219-4225.
11. All new nonpolymeric compounds were characterized by NMR, IR, MS, and HRMS. The purity was determined using GC, GC-MS, and NMR techniques. Polymeric compounds were characterized using IR and elemental analysis (CHN) (see the Experimental Procedures section).
12. Zimmermann, V.; Avemaria, F.; Bräse, S. J. Comb. Chem. 2007, 9, 200-203.
13. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413-2416.
14. (a) Avemaria, F.; Zimmermann, V.; Bräse, S. Synlett 2004, 1163-1166.
15. (b) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. 2005, 777, 5320-5374.
16. (c) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188-5240.
17. Kaczmarek, L.; Luniewski, W.; Zagrodzki, B.; Godlewska, J.; Osiadacz, J.; Wietrzyk, J.; Opolski, A.; Peczynska-Czoch, W. Acta Pol. Pharm. 2002, 59 (3), 199-207.
18. Battra, M.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron 1990, 46, 587-594.
19. 2Cb results in formation of highly explosive methylene azides. See ref 12b.
20. Schoepff, M. Chem. Calc. 1890, 23, 1843.
21. Borsche, W.; Feise, M. Chem. Calc. 1907, 40, 384.
22. Kulagowski, J. J.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Perkin Trans, 1 1985, 2725-2732.
23. Lambert, P.-H.; Bertin, S.; Lacoste, J.-M.; Volland, J.-P.; Krick, A.; Furet, E.; Botrel, A.; Guenot, P. J. Mass. Spectrom. 1998, 33, 242-249.
24. Lawson; Perkin; Robinson, J. Chem. Soc. [London] 1924, 653.
25. Holt, S. J.; Petrow, V. J. Chem. Soc. [London] 1948, 922.
26. Peczynska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratynski, J. J. Med. Chem. 1994, 37, 3503-3510.