Synthesis of 3-iodoindoles by the Pd/Cu-catalyzed coupling of N,N-dialkyl-2-iodoanilines and terminal acetylenes, followed by electrophilic cyclization

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 62-69

  Yue, Dawei ^a   Yao, Tuanli ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ELECTROPHORESIS; PALLADIUM; SYNTHESIS (CHEMICAL);

CARBON-NITROGEN BOND; CYCLIZATION; HECK REACTIONS;

IODINE COMPOUNDS;

2 IODOANILINE; 3 IODOINDOLE; ACETYLENE; ALKYL GROUP; ANILINE DERIVATIVE; COPPER; INDOLE DERIVATIVE; PALLADIUM; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; SONOGASHIRA REACTION; SUZUKI REACTION; SYNTHESIS;

ACETYLENE; ALKYLATION; ANILINE COMPOUNDS; CATALYSIS; COPPER; CYCLIZATION; ELECTRONS; INDOLES; IODINE; MOLECULAR STRUCTURE; PALLADIUM;

EID: 31144470445     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051549p     Document Type: Article

References (55)

1. For reviews, see: (a) Sundberg, R. J. Prog. Heterocycl. Chem. 1989, 1, 111.
2. (b) Saxton, J. E. Nat. Prod. Rep. 1986, 3, 357;
3. Nat. Prod. Rep. 1987, 4, 591;
4. Nat. Prod. Rep. 1989, 6, 1.
5. (c) Sundberg, R. J. Indoles; Academic Press: New York, 1996.
6. (d) Mori, H.; Yoshimi, N. Mutat. Res. 2001, 480, 201.
7. (e) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
8. (f) Toyota, M.; Ihara, M. Nat. Prod. Rep. 1998, 15, 327.
9. (g) Lobo, A. M.; Prabhakar, S. J. Heterocycl. Chem. 2002, 39, 429.
10. (h) Tokuyama, H.; Fukuyama, T. Kagaku Kogyo 2001, 52, 416.
11. (i) Xiong, W. N.; Yang, C. G.; Jiang, B. Bioorg. Med. Chem. 2001, 9, 1773.
12. (j) Ezquerra, J.; Pedregal, C.; Lamas, C. J. Org. Chem. 1996, 61, 5804.
13. (a) Sonada, T.; Kawakami, M.; Ikeda, T.; Kobayashi, S.; Taniguchi, H. J. Chem. Soc., Chem. Commun. 1976, 612.
14. (b) Kitamura, T.; Kobayashi, S.; Taniguchi, H.; Hori, K. J. Am. Chem. Soc. 1991, 113, 6240.
15. (c) Kitamura, T.; Takachi, T.; Kawasato, H.; Taniguchi, H. J. Chem. Soc., Perkin Trans. 1 1992, 1969.
16. (a) Larock, R. C.; Yue, D. Tetrahedron Lett. 2001, 42, 6011.
17. (b) Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905.
18. (c) Flynn, B. L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 3, 651.
19. (a) Huang, Q.; Hunter, J. A.; Larock, R. C. Org. Lett. 2001, 3, 2973.
20. (b) Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437.
21. (a) Yao, T.; Larock, R. C. Tetrahedron Lett. 2002, 43, 7401.
22. (b) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936.
23. (c) Oliver, M. A.; Gandour, R. D. J. Org. Chem. 1984, 49, 558.
24. (d) Biagetti, M.; Bellina, F.; Carpita, A.; Stabile, P.; Rossi, R. Tetrahedron 2002, 58, 5023.
25. (e) Rossi, R.; Carpita, A.; Bellina, F.; Stabile, P.; Mannina, L. Tetrahedron 2003, 59, 2067.
26. Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432.
27. (a) Bew, S. P.; Knight, D. W. J. Chem. Soc., Chem. Commun. 1996, 1007.
28. (b) Djuardi, E.; McNelis, E. Tetrahedron Lett. 1999, 40, 7193.
29. (c) El-Taeb, G. M. M.; Evans, A. B.; Jones, S.; Knight, D. W. Tetrahedron Lett. 2001, 42, 5945.
30. (d) Rao, M. S.; Esho, N.; Sergeant, C.; Dembinski, R. J. Org. Chem. 2003, 68, 6788.
31. (e) Sniady, A.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2005, 7, 1769.
32. (f) Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164.
33. (a) Barluenga, J.; Trincado, M.; Rubio, E.; Gonzalez, J. M. Angew. Chem., Int. Ed. 2003, 42, 2406.
34. (b) Yue, D.; Larock, R. C. Org. Lett. 2004, 6, 1037.
35. (c) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2004, 45, 539.
36. Arcadi, A.; Cacchi, S.; Di Giuseppe, S.; Fabrizi, G.; Marinelli, F. Org. Lett. 2002, 4, 2409.
37. Marshall, J. A.; Yanik, M. M. J. Org. Chem. 1999, 64, 3798.
38. Knight, D. W.; Redfern, A. L.; Gilmore, J. J. Chem. Soc., Chem. Commun. 1998, 2207.
39. (a) Barluenga, J.; Vazque-Villa, H.; Ballestems, A.; Gonzaléz, J. M. J. Am. Chem. Soc. 2003, 125, 9028.
40. (b) Barluenga, J.; Vazque-Villa, H.; Ballestems, A.; Gonzaléz, J. M. Org. Lett. 2003, 5, 4121.
41. (c) Yue, D.; Della Cá, N.; Larock, R. C. Org. Lett. 2004, 6, 1581.
42. Ren, X.-F.; Konaklieva, M. I.; Shi, H.; Dickey, S.; Lim, D. V.; Gonzaléz, J.; Turos, E. J. Org. Chem. 1998, 63, 8898.
43. (a) Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
44. (b) Nakamura, H.; Ohtaka, M.; Yamamoto, Y. Tetrahedron Lett. 2002, 43, 7631.
45. (c) Yue, D.; Della Cá, N.; Larock, R. C. Org. Lett. 2004, 6, 1581.
46. Peng, A.-Y.; Ding, Y.-X. Org. Lett. 2004, 6, 1119.
47. Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 1432.
48. Barluenga, J.; Trincado, M.; Marco-Arias, M.; Ballesteros, A.; Rubio, E.; Gonzalez, J. M. Chem. Commun. 2005, 2008.
49. For a review, see: Nevado, C.; Echavarren, A. M. Synthesis 2005, 167.
50. Ten Hoedt, R. W. M.; Van Koten, G.; Noltes, J. G. Synth. Commun. 1977, 7, 61.
51. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 5, pp 203-229.
52. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
53. Cadogan, J. T. G.; Hickson, C. L.; Husband, J. B.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1985, 1891.
54. Bumagin, N.; Bykov, V. V. Tetrahedron 1997, 53, 14437.
55. Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.