Palladium-catalyzed tandem alkenyl and aryl C-N bond formation: A cascade N-annulation route to 1-functionalized indoles

Angewandte Chemie - International Edition

Volumn 44, Issue 3, 2005, Pages 403-406

  Willis, Michael C ^a   Brace, Gareth N ^a   Holmes, Ian P ^b  

^a University of Bath Claverton Down   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Amination; Cascade reactions; Indoles; Nitrogen heterocycles; Palladium

Indexed keywords

CATALYSIS; CHEMICAL BONDS; PALLADIUM; REACTION KINETICS;

BOND FORMING REACTIONS; INDOLES; SULFOAMIDES; TANDEM OPERATIONS;

NITROGEN COMPOUNDS;

ALKENYL GROUP; CARBON; INDOLE DERIVATIVE; NITROGEN;

AMINATION; ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; SUBSTITUTION REACTION;

CARBON; CATALYSIS; INDOLES; NITROGEN; PALLADIUM;

EID: 12344275854     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461598     Document Type: Article

References (38)

1. For reviews on indoles, see: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045.
2. For reviews on indoles, see: a) R. J. Sundberg, Indoles, Academic Press, London, 1996; b) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045.
3. a) J. J. Li, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon, Amsterdam, 2000;
4. b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127.
5. For reviews, see: a) S. Cacchi, F. Marinelli in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2 (Ed.: E.-I. Negishi), Wiley, New York, 2002, p 2227; b) G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285.
6. For reviews, see: a) S. Cacchi, F. Marinelli in Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2 (Ed.: E.-I. Negishi), Wiley, New York, 2002, p 2227; b) G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285.
7. For selected recent examples, see: a) K. Aoki, A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 3068; b) J. A. Brown, Tetrahedron Lett. 2000, 41, 1623; c) K. Yamazaki, Y. Nakamura, Y. Kondo, J. Org. Chem. 2003, 68, 6011; d) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. 2003, 115, 3151; Angew. Chem. Int. Ed. 2003, 42, 3042.
8. For selected recent examples, see: a) K. Aoki, A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 3068; b) J. A. Brown, Tetrahedron Lett. 2000, 41, 1623; c) K. Yamazaki, Y. Nakamura, Y. Kondo, J. Org. Chem. 2003, 68, 6011; d) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. 2003, 115, 3151; Angew. Chem. Int. Ed. 2003, 42, 3042.
9. For selected recent examples, see: a) K. Aoki, A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 3068; b) J. A. Brown, Tetrahedron Lett. 2000, 41, 1623; c) K. Yamazaki, Y. Nakamura, Y. Kondo, J. Org. Chem. 2003, 68, 6011; d) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. 2003, 115, 3151; Angew. Chem. Int. Ed. 2003, 42, 3042.
10. For selected recent examples, see: a) K. Aoki, A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 3068; b) J. A. Brown, Tetrahedron Lett. 2000, 41, 1623; c) K. Yamazaki, Y. Nakamura, Y. Kondo, J. Org. Chem. 2003, 68, 6011; d) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. 2003, 115, 3151; Angew. Chem. Int. Ed. 2003, 42, 3042.
11. For selected recent examples, see: a) K. Aoki, A. J. Peat, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 3068; b) J. A. Brown, Tetrahedron Lett. 2000, 41, 1623; c) K. Yamazaki, Y. Nakamura, Y. Kondo, J. Org. Chem. 2003, 68, 6011; d) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. 2003, 115, 3151; Angew. Chem. Int. Ed. 2003, 42, 3042.
12. S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251.
13. For examples, see: a) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575; b) D. W. Old, M. C. Harris, S. L. Buchwald, Org. Lett. 2000, 2, 1403; c) E. M. Beccalli, G. Broggini, Tetrahedron Lett. 2003, 44, 1919; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578.
14. For examples, see: a) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575; b) D. W. Old, M. C. Harris, S. L. Buchwald, Org. Lett. 2000, 2, 1403; c) E. M. Beccalli, G. Broggini, Tetrahedron Lett. 2003, 44, 1919; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578.
15. For examples, see: a) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575; b) D. W. Old, M. C. Harris, S. L. Buchwald, Org. Lett. 2000, 2, 1403; c) E. M. Beccalli, G. Broggini, Tetrahedron Lett. 2003, 44, 1919; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578.
16. For examples, see: a) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575; b) D. W. Old, M. C. Harris, S. L. Buchwald, Org. Lett. 2000, 2, 1403; c) E. M. Beccalli, G. Broggini, Tetrahedron Lett. 2003, 44, 1919; d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578.
17. For recent reviews on Pd-catalyzed C-O and C-N bond formation, see: a) J. F. Hartwig in Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; b) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131; c) D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041.
18. For recent reviews on Pd-catalyzed C-O and C-N bond formation, see: a) J. F. Hartwig in Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; b) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131; c) D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041.
19. For recent reviews on Pd-catalyzed C-O and C-N bond formation, see: a) J. F. Hartwig in Modern Amination Methods (Ed.: A. Ricci), Wiley-VCH, Weinheim, 2000; b) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131; c) D. Prim, J.-M. Campagne, D. Joseph, B. Andrioletti, Tetrahedron 2002, 58, 2041.
20. a) M. C. Willis, G. N. Brace, Tetrahedron Lett. 2002, 43, 9085;
21. b) J. Barluenga, M. A. Fernández, F. Aznar, C. Valdés, Chem. Commun. 2002, 2362;
22. c) D. B. Wallace, D. J. Klauber, C.-y. Chen, R. P. Volante, Org. Lett. 2003, 5, 4749.
23. For a carbazole synthesis that involves tandem palladium-catalyzed aryl C-N bond formation, see: K. Nozaki, K. Takahashi, K. Nakano, T. Hiyama, H.-Z. Tang, M. Fujiki, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2097; Angew. Chem. Int. Ed. 2003, 42, 2051.
24. For a carbazole synthesis that involves tandem palladium-catalyzed aryl C-N bond formation, see: K. Nozaki, K. Takahashi, K. Nakano, T. Hiyama, H.-Z. Tang, M. Fujiki, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2097; Angew. Chem. Int. Ed. 2003, 42, 2051.
25. For N-arylated indoles, see: a) G. Spadoni, C. Balsamini, A. Bedini, G. Diamantini, B. Di Giacomo, A. Tontini, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, R. Nonno, M. Pannacci, V. Lucini, F. Frachini, B. M. Stankov, J. Med. Chem. 1998, 41, 3624; b) K. Andersen, T. Liljefors, J. Hyttel, J. Perregaard, J. Med. Chem. 1996, 39, 3723; c) C. A. Harbert, J. J. Plattner, W. M. Welch, J. Med. Chem. 1980, 23, 635.
26. For N-arylated indoles, see: a) G. Spadoni, C. Balsamini, A. Bedini, G. Diamantini, B. Di Giacomo, A. Tontini, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, R. Nonno, M. Pannacci, V. Lucini, F. Frachini, B. M. Stankov, J. Med. Chem. 1998, 41, 3624; b) K. Andersen, T. Liljefors, J. Hyttel, J. Perregaard, J. Med. Chem. 1996, 39, 3723; c) C. A. Harbert, J. J. Plattner, W. M. Welch, J. Med. Chem. 1980, 23, 635.
27. For N-arylated indoles, see: a) G. Spadoni, C. Balsamini, A. Bedini, G. Diamantini, B. Di Giacomo, A. Tontini, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, R. Nonno, M. Pannacci, V. Lucini, F. Frachini, B. M. Stankov, J. Med. Chem. 1998, 41, 3624; b) K. Andersen, T. Liljefors, J. Hyttel, J. Perregaard, J. Med. Chem. 1996, 39, 3723; c) C. A. Harbert, J. J. Plattner, W. M. Welch, J. Med. Chem. 1980, 23, 635.
28. 2NPh, Scheme 2). See Supporting Information for details.
29. J. Yin, M. P. Rainka, X.-X. Zhang, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 1162.
30. M. Kranenburg, Y. E. M. van der Burgt, P. C. J. Kamer, P. W. N. M. van Leeuwen, K. Goubitz, J. Fraanje, Organometallics 1995, 14, 3081.
31. See Supporting Information for details.
32. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176.
33. A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350; Angew. Chem. Int. Ed. 2002, 41, 4176.
34. a) J. M. Fox, X. Huang, A. Chieffi, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 1360;
35. b) D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234;
36. c) M. S. Viciu, R. F. Germaneau, S. P. Nolan. Org. Lett. 2002, 4, 4053.
37. For an indole synthesis that commences with the arylation of ketones with o-halonitroarenes, see: J. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168.
38. 2O).