One-Pot Synthesis of Polyheterocycles by a Palladium-Catalyzed Intramolecular N-Arylation/C-H Activation/Aryl-Aryl Bond-Forming Domino Process

Angewandte Chemie - International Edition

Volumn 42, Issue 39, 2003, Pages 4774-4777

  Cuny, Guylaine ^a   Bois Choussy, Michèle ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

C C coupling; C H activation; Cyclization; Domino reactions; Palladium

Indexed keywords

CATALYSIS; CHEMICAL BONDS; SYNTHESIS (CHEMICAL);

CATALYTIC DOMINO REACTIONS;

ORGANIC POLYMERS;

HETEROCYCLIC COMPOUND; PALLADIUM; POLYHETEROCYCLIC DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BINDING; CYCLIZATION; HEATING; LIGAND BINDING; METAL BINDING; MOLECULAR BIOLOGY; PROCESS DEVELOPMENT; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0142183595     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351923     Document Type: Article

References (62)

1. Reviews: a) C. J. Roxburgh, Tetrahedron 1995, 51, 9767-9822;
2. b) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452;
3. c) J. Zhu, Synlett 1997, 133-144;
4. d) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
5. d) A. Fürstner, Angew. Chem. 2000, 112, 3140-3172; Angew. Chem. Int. Ed. 2000, 39, 3012-3043;
6. e) K. E. Krakowiak, R. M. Izatt, J. S. Bradshaw, J. Heterocycl. Chem. 2001, 38, 1239-1248;
7. Recent examples from this group: f) G. Zhao, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2001, 123, 6700-6701;
8. g) P. Janvier, M. Bois-Choussy, H. Bienaymé, J. Zhu, Angew. Chem. 2003, 115, 845-847; Angew. Chem. Int. Ed. 2003, 42, 811-814, and references therein.
9. g) P. Janvier, M. Bois-Choussy, H. Bienaymé, J. Zhu, Angew. Chem. 2003, 115, 845-847; Angew. Chem. Int. Ed. 2003, 42, 811-814, and references therein.
10. A. C. Carbonnelle, J. Zhu, Org. Lett. 2000, 2, 3477-3480.
11. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
12. a) J. P. Wolfe, S. Wagaw, J. F. Marcoux, S. F. Buchwald, Acc. Chem. Res. 1998, 31, 805-818;
13. b) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125-146.
14. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
15. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
16. b) J. F. Hartwig in Modern Amination Methods (Ed. A. Ricci), Wiley-VCH, Weinheim, 2000, Chap. 7.
17. a) L. F. Tietze, Chem. Rev. 1996, 96, 115-136;
18. b) A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-269.
19. Reviews: a) G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1698-1712;
20. Reviews: a) G. Dyker, Angew. Chem. 1999, 111, 1808-1822; Angew. Chem. Int. Ed. 1999, 38, 1698-1712;
21. b) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769;
22. c) M. Catellani, Synlett 2003, 298-313;
23. Recent examples: d) Harayama, T. K. Shibaike, Heterocycles 1998, 49, 191-195;
24. e) T. Harayama, T. Akiyama, H. Akamatsu, K. Kawano, H. Abe, Y. Takeuchi, Synthesis 2001, 3, 444-450;
25. f) T. Harayama, T. Akiyama, Y. Nakano, H. Nishioka, H. Abe, Y. Takeuchi, Chem. Pharm. Bull. 2002, 50, 519-522;
26. g) F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698-1699;
27. h) A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto, T. Ikeda, J. Am. Chem. Soc. 2003, 125, 1700-1701.
28. a) J. P. Wolfe, R. A. Rennels, S. L. Buchwald, Tetrahedron 1996, 52, 7525-7546;
29. b) S. Wagaw, R. A. Rennels, S. L. Buchwald, J. Am. Chem. Soc. 1997, 119, 8451-8458;
30. c) B. H. Yang, S. L. Buchwald, Org. Lett. 1999, 1, 35-37;
31. d) A. Abouabdellah, R. H. Dodd, Tetrahedron Lett. 1998, 39, 2119-2122;
32. e) K. Yamada, T. Kubo, H. Tokuyama, T. Fukuyama, Synlett 2002, 231-234;
33. f) M. Qadir, R. E. Priestley, T. W. D. F. Rising, T. Gelbrich, S. J. Coles, M. B. Hursthouse, P. W. Sheldrake, N. Whittall, K. K. Hii, Tetrahedron Lett. 2003, 44, 3675-3678;
34. g) G. Evindar, R. A. Batey, Org. Lett. 2003, 5, 133-136;
35. h) B. J. Margolis, J. J. Swidorski, B. N. Rogers, J. Org. Chem. 2003, 68, 644-647;
36. i) K. Nozaki, K. Takahashi, K. Nakano, T. Hiyama, H. Z. Tang, M. Fujiki, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2097-2099; Angew. Chem. Int. Ed. 2003, 42, 2051-2053;
37. i) K. Nozaki, K. Takahashi, K. Nakano, T. Hiyama, H. Z. Tang, M. Fujiki, S. Yamaguchi, K. Tamao, Angew. Chem. 2003, 115, 2097-2099; Angew. Chem. Int. Ed. 2003, 42, 2051-2053;
38. j) R. Omar-Amrani, A. Thomas, E. Brenner, R. Schneider, Y. Fort, Org. Lett. 2003, 5, 2311-2314.
39. For an elegant application in natural product synthesis, see F. He, B. M. Foxman, B. B. Snider, J. Am. Chem. Soc. 1998, 120, 6417-6418.
40. 3P as ligand: M. K. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2003, 68, 2861-2873. For a recent review, see A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
41. 3P as ligand: M. K. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2003, 68, 2861-2873. For a recent review, see A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
42. 3P as ligand: M. K. Hooper, M. Utsunomiya, J. F. Hartwig, J. Org. Chem. 2003, 68, 2861-2873. For a recent review, see A. F. Littke, G. C. Fu, Angew. Chem. 2002, 114, 4350-4386; Angew. Chem. Int. Ed. 2002, 41, 4176-4211.
43. S. L. Schreiber, Science 2000, 287, 1964-1968.
44. a) S. Bräse, C. Gil, K. Knepper, Bioorg. Med. Chem. 2002, 10, 2415-2437;
45. b) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51-80;
46. c) D. A. Horton, G. T. Bourne, M. L. Smythe, Chem. Rev. 2003, 103, 893-930.
47. "Ligand-free" palladium-catalyzed cross-coupling reaction: a) Review: I. P. Beletskaya, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1991, 40, 2013-2028;
48. Recent examples: b) T. I. Wallow, B. M. Novak, J. Org. Chem. 1994, 59, 5034-5037;
49. c) M. Moreno-Mañas, F. Pajuelo, R. Pleixats, J. Org. Chem. 1995, 60, 2396-2397;
50. d) D. Badone, M. Baroni, R. Cardamone, A. Ielmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170-7173;
51. e) C. G. Blettner, W. A. König, W. Stenzel, T. Schotten, J. Org. Chem. 1999, 64, 3885-3890;
52. f) N. E. Leadbeater, M. Marco, Org. Lett. 2002, 4, 2973-2976;
53. g) R. B. Bedford, M. E. Blake, C. P. Butts, D. Holder, Chem. Commun. 2003, 466-467.
54. a) G. M. Whitesides, J. F. Gaasch, E. R. Stedronsky, J. Am. Chem. Soc. 1972, 94, 5258-5270;
55. b) J. F. Hartwig, S. Richards, D. Baranãno, F. Paul, J. Am. Chem. Soc. 1996, 118, 3626-3633;
56. c) J. F. Marcoux, S. Wagaw, S. L. Buchwald, J. Org. Chem. 1997, 62, 1568-1569.
57. DMFas ligand: a) J. M. Gioria, B. P. Susz, Helv. Chim. Acta 1971, 54, 2251-2256;
58. b) C. Amatore, A. A. Bahsoun, A. Jutand, G. Meyer, A. N. Ntepe, L. Richard, J. Am. Chem. Soc. 2003, 125, 4212-4222.
59. It is also possible that the formation of an Ar-Pd-Ar' intermediate proceeded Ar-N bond formation, as proposed by one of the referees. We are further investigating this mechanistic issue.
60. Intermolecular N-arylation followed by aryl-aryl bond formation leading to five-membered carbazoles was recently reported: R. B. Bedford, S. J. Cazin, Chem. Commun. 2002, 2310-2311. Sequential intra- and intermolecular N-arylation leading to functionalized 1-aminoindoles: M. Watanabe, T. Yamamoto, M. Nishiyama, Angew. Chem. 2000, 112, 2620-2623; Angew. Chem. Int. Ed. 2000, 39, 2501-2504.
61. Intermolecular N-arylation followed by aryl-aryl bond formation leading to five-membered carbazoles was recently reported: R. B. Bedford, S. J. Cazin, Chem. Commun. 2002, 2310-2311. Sequential intra- and intermolecular N-arylation leading to functionalized 1-aminoindoles: M. Watanabe, T. Yamamoto, M. Nishiyama, Angew. Chem. 2000, 112, 2620-2623; Angew. Chem. Int. Ed. 2000, 39, 2501-2504.
62. Intermolecular N-arylation followed by aryl-aryl bond formation leading to five-membered carbazoles was recently reported: R. B. Bedford, S. J. Cazin, Chem. Commun. 2002, 2310-2311. Sequential intra- and intermolecular N-arylation leading to functionalized 1-aminoindoles: M. Watanabe, T. Yamamoto, M. Nishiyama, Angew. Chem. 2000, 112, 2620-2623; Angew. Chem. Int. Ed. 2000, 39, 2501-2504.