Gold-catalyzed intramolecular reaction of indoles with alkynes: Facile formation of eight-membered rings and an unexpected allenylation

Angewandte Chemie - International Edition

Volumn 45, Issue 7, 2006, Pages 1105-1109

  Ferrer, Catalina ^a   Echavarren, Antonio M ^a,b  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Alkynes; Allenes; Cyclization; Gold; Indoles

Indexed keywords

CATALYSIS; COMPLEXATION; GOLD; REACTION KINETICS;

ALKYNES; ALLENES; CYCLIZATION; INDOLES;

ORGANIC COMPOUNDS;

EID: 33746081826     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200503484     Document Type: Article

References (52)

1. Review: C. Nevado, A. M. Echavarren, Synthesis 2005, 167-182.
2. M. Reetz, K. Sommer, Eur. J. Org. Chem. 2003, 3485-3496.
3. Z. Shi, C. He, J. Org. Chem. 2004, 69, 3669-3671.
4. N. Chatani, H. Inoue, T. Ikeda, S. Murai, J. Org. Chem. 2000, 65, 4913-4918.
5. H. Inoue, N. Chatani, S. Murai, J. Org. Chem. 2002, 67, 1414-1417.
6. 3 only takes place with phenylacetylene to give 1,1-bis(1H-3-indolyl)-1-phenylethanes: J. S. Yadav, B. V. S. Reddy, B. Padmavani, M. K. Gupta, Tetrahedron Lett. 2004, 45, 7577-7579.
7. a) A. Fürstner, V. Mamame, J. Org. Chem. 2002, 67, 6264-6267;
8. b) A. Fürstner, V. Mamame, Chem. Commun. 2003, 2112-2113;
9. c) V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556-4575.
10. a) S. J. Pastine, S. W. Youn, D. Sames, Org. Lett. 2003, 5, 1055-1058;
11. h) S. J. Pastine, S. W. Youn, D. Sames, Tetrahedron 2003, 59, 8859-8868.
12. M. Nishizawa, H. Takao, V. K. Yadav, H. Imagawa, T. Sugihara, Org. Lett. 2003, 5, 4563-4565.
13. L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 10 204-10 205.
14. C. Nevado, A. M. Echavarren, Chem. Eur. J. 2005, 11, 3155-3164.
15. C. Nieto-Oberhuber, M. P. Muñoz, E. Buñuel, C. Nevado, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. 2004, 116, 2456-2460;
16. Angew. Chem. Int. Ed. 2004, 43, 2402-2406.
17. For recent transition-metal-catalyzed annulations of indoles, see: a) E. M. Beccalli, C. Broggini, Tetrahedron Lett. 2003, 44, 1919-1921;
18. b) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578-9579;
19. c) C. Liu, X. Han, X. Wang, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 3700-3701;
20. d) C. Liu, R. A. Widenhoefer, J. Am. Chem. Soc. 2004, 126, 10 250-10 251;
21. e) C. Bressy, D. Alberico, M. Lautens, J. Am. Chem. Soc. 2005, 127, 13 148-13 149;
22. f) B. A. Bhanu Prasad, F. K. Yoshimoto, R. Sarpong, J. Am. Chem. Soc. 2005, 127, 12 468-12 469;
23. g) for a review on palladium-catalyzed synthesis and functionalization of indoles, see: S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920.
24. For a recent review on indolic natural products, see: M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73-103.
25. 3, see: a) A. S. K. Hashmi, T. M. Frost, J. W. Bats, J. Am. Chem. Soc. 2000, 122, 11 553-11 554;
26. b) A. S. K. Hashmi, T. M. Frost, J. W. Bats, Org. Lett. 2001, 3, 3769-3771;
27. c) C. Nevado, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2003, 9, 2627-2635;
28. d) A. S. K. Hashmi, L. Ding, J. W. Bats, P. Fischer, W. Frey, Chem. Eur. J. 2003, 9, 4339-4345;
29. e) A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. 2004, 116, 6707-6709;
30. Angew. Chem. Int. Ed. 2004, 43, 6545-6547;
31. f) A. S. K. Hashmi, M. Rudolph, J. P. Weyrauch, M. Wölfle, W. Frey, J. W. Bats, Angew. Chem. 2005, 117, 2858-2861;
32. Angew. Chem. Int. Ed. 2005, 44, 2798-2801.
33. 8] to give 1,3-cyclooctadienes, see: H. Kagoshima, M. Hayashi, Y. Hashimoto, K. Saigo, Organometallics 1996, 15, 5439-5441.
34. We have observed a different stereochemical outcome depending on the oxidation state of the palladium catalyst in the cyclization of allylstannanes with alkynes: B. Martín-Matute, E. Buñuel, D. J. Cárdenas, M. Méndez, C. Nieto-Oberhuber, A. M. Echavarren, J. Organomet. Chem. 2003, 687, 410-419.
35. a) P. S. Steyn, Tetrahedron Lett. 1971, 3331-3334;
36. b) P. S. Steyn, Tetrahedron 1973, 107-120;
37. c) P. G. Sames, Fortschr. Chem. Org. Naturst. 1975, 32, 51-117.
38. Synthesis of 4 and related alkaloids: P. S. Baran, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 7904-7905.
39. Synthesis of 5: P. S. Baran, C. A. Guerrero, E. J. Corey, J. Am. Chem. Soc. 2003, 125, 5628-5629.
40. T.-S. Kam, K.-H. Lim, K. Yoganathan, M. Hayashi, K. Komiyama, Tetrahedron 2004, 60, 10 739-10 745.
41. For indoloazocines as intermediates in the synthesis of other indole alkaloids, see: M. E. Kuehne, S. D. Cowen, F. Xu, L. S. Borman, J. Org. Chem. 2001, 66, 5303-5316.
42. Synthesis of indoloazocines: L. G. Voskressensky, T. N. Borisova, L. N. Kulikova, A. V. Varlamov, M. Catto, C. Altomare, A. Carotti, Eur. J. Org. Chem. 2004, 3128-3135, and references therein.
43. C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
44. C. Nieto-Oberhuber, S. López, M. P. Muñoz, D. J. Cárdenas, E. Buñuel, C. Nevado, A. M. Echavarren, Angew. Chem. 2005, 117, 6302-6304;
45. Angew. Chem. Int. Ed. 2005, 44, 6146-6148.
46. 1 complexes will be reported separately.
47. S. K. Hashmi, J. P. Weyrauch, W. Frey, J. W. Bats, Org. Lett. 2004, 6, 4391-4394.
48. Involvement of 3,3-disubstituted indolenines in 1,2-migrations to form indoles: a) A. H. Jackson, P. Smith, Chem. Commun. 1967, 264-266;
49. b) A. H. Jackson, P. Smith, Tetrahedron 1968, 24, 403-413;
50. c) A. H. Jackson, P. Smith, Tetrahedron 1968, 24, 2227-2239;
51. d) A. Ganesan, C. H. Heathcock, Tetrahedron Lett. 1993, 34, 439-440.
52. For a recent review on synthetic applications of allenes, see: S.-M. Ma, Chem. Rev. 2005, 105, 2829-2872.