Combined C-H functionalization/C-N bond formation route to carbazoles

Journal of the American Chemical Society

Volumn 127, Issue 42, 2005, Pages 14560-14561

  Tsang, W C Peter ^a   Zheng, Nan ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETAMINOBIPHENYL; CARBAZOLE DERIVATIVE; CARBON; COPPER; HYDROGEN; N ACETYLCARBAZOLE; NITROGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COVALENT BOND; OXIDATION; REACTION ANALYSIS; STOICHIOMETRY; SUZUKI REACTION;

CARBAZOLES; CARBON; CYCLIZATION; HYDROGEN; MOLECULAR STRUCTURE; NITROGEN;

EID: 27144450136     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055353i     Document Type: Article

References (35)

1. Brown, E. G. Ring Nitrogen and Key Biomolecules; Kluwer: Boston, MA, 1998.
2. Li, J.-J., Corey, E. J., Eds. Name Reactions in Heterocyclic Chemistry; Wiley-Interscience: Hoboken, NJ, 2005.
3. (a) Nozaki, K.; Takahashi, K.; Nakano, K.; Hiyama, T.; Tang, H.-Z.; Fujiki, M.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2051.
4. (b) Grazulevicius, J. V.; Strohriegl, P.; Pielichowski, J.; Pielichowski, K. Prog. Polym. Sci. 2003, 28, 1297.
5. (c) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
6. (d) Thomas, K. R. J.; Lin, J. T.; Tao, Y.-T.; Ko, C.-W. J. Am. Chem. Soc. 2001, 123, 9404.
7. (e) Zhang, Y.; Wada, T.; Sasabe, H. J. Mater. Chem. 1998, 8, 809.
8. (f) Chakraborty, D. P. The Alkaloids 1993, 44, 257.
9. For recent reviews of Pd- or Cu-catalyzed carbon-heteroatom bond formation processes, see: (a) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 2004; p 699.
10. (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
11. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
12. (d) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051.
13. For recent examples of directed C-H functionalization/C-C bond-forming reactions, see: (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
14. (b) Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192.
15. (c) Orito, K.; Horibata, A.; Nakamura, T.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Tokuda, M. J. Am. Chem. Soc. 2004, 126, 14342.
16. (d) Kakiuchi, F.; Kan, S.; Igi, K.; Chantani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
17. (e) Dangel, B. D.; Godula, K.; Youn, S. W.; Sezen, B.; Sames, D. J. Am. Chem. Soc. 2002, 124, 11856.
18. For recent reviews of C-H functionalization/C-C bond-forming reactions, see: (a) Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077.
19. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
20. (c) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
21. (d) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
22. (e) Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992.
23. (f) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1699.
24. (a) Brice, J. L.; Harang, J. E.; Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868.
25. (b) Timokhin, V. I.; Anastasi, N. R.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 12996.
26. For recent reviews of nitrene insertions into alkyl C-H bonds, see: (a) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 2.
27. (b) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
28. (a) Tremont, S. J.; Rahman, H. U. J. Am. Chem. Soc. 1984, 106, 5759.
29. (b) McCallum, J. S.; Gasdaska, J. R.; Liebeskind, L. S.; Tremont, S. J. Tetrahedron Lett. 1989, 30, 4085.
30. (a) Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156.
31. (b) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
32. (c) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
33. (a) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
34. (b) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
35. Jira, R. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: New York, 2002; Vol. 1, p 386.