Gold(I)-catalyzed tandem reactions initiated by 1,2-indole migrations

Angewandte Chemie - International Edition

Volumn 47, Issue 38, 2008, Pages 7354-7357

  Sanz, Roberto ^a   Miguel, Delia ^a   Rodríguez, Félix ^b  

^a UNIVERSITY OF BURGOS   (Spain)

^b UNIVERSITY OF OVIEDO   (Spain)

Author keywords

C C coupling; Cyclization; Gold; Homogeneous catalysis; Indoles

Indexed keywords

CHEMICAL REACTIONS;

C-C COUPLING; CYCLIZATION; GOLD; HOMOGENEOUS CATALYSIS; INDOLES;

GOLD COMPOUNDS;

EID: 53249094195     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802660     Document Type: Article

References (59)

1. For recent reviews on gold catalysis, see: a) N. Bongers, N. Krause, Angew. Chem. 2008, 120, 2208-2211;
2. Angew. Chem. Int. Ed. 2008, 47, 2178-2181;
3. b) J. Muzart, Tetrahedron 2008, 64, 5815-5849;
4. c) H. C. Shen, Tetrahedron 2008, 64, 3885-3903;
5. d) D. J. Gorin, D. Toste, Nature 2007, 446, 395-403;
6. e) A. Fürstner, P. W. Davies, Angew. Chem. 2007, 119, 3478-3519;
7. Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
8. f) E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346;
9. g) A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
10. h) L. Zhang, J. Sun, S. A. Kozmin, Adv. Synth. Catal. 2006, 348, 2271-2296;
11. i) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105;
12. Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
13. j) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555-4563;
14. k) A. Hoffmann-Róder, N. Krause, Org. Biomol. Chem. 2005, 3, 387-391;
15. l) A. S. K. Hashmi, Gold Bull. 2004, 37, 51-65.
16. For excellent accounts see the following and references therein: a) A. Correa, N. Marion, L. Fensterbank, M. Malacria, S. P. Nolan, L. Cavallo, Angew. Chem. 2008, 120, 730-733;
17. Angew. Chem. Int. Ed. 2008, 47, 718-721;
18. b) N. Marion, S. P. Nolan, Angew. Chem. 2007, 119, 2806-2809;
19. Angew. Chem. Int. Ed. 2007, 46, 2750-2752;
20. c) J. Marco-Contelles, E. Soriano, Chem. Eur. J. 2007, 13, 1350-1357.
21. For some leading works involving 1,2-acyl migrations promoted by gold complexes, see: a) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
22. b) X. Shi, D. J. Gorin, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 5802-5803;
23. c) M. J. Johansson, D. J. Gorin, S. T. Staben, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 18002-18003;
24. d) C. H. M. Amijs, V. López-Carrillo, A. M. Echavarren, Org. Lett. 2007, 9, 4021-4024;
25. e) D. J. Gorin, I. D. G. Watson, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 3736-3737;
26. f) G. Li, G. Zhang, L. Zhang, J. Am. Chem. Soc. 2008, 130, 3740-3741.
27. L. Peng, X. Zhang, S. Zhang, J. Wang, J. Org. Chem. 2007, 72, 1192-1197.
28. For a gold-catalyzed 1,2-alkyl and -aryl migration in allenyl ketones, see: A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2007, 119, 5287-5289;
29. Angew. Chem. Int. Ed. 2007, 46, 5195-5197.
30. a) R. Sanz, A. Martínez, J. M. Álvarez-Gutiérrez, F. Rodríguez, Eur. J. Org. Chem. 2006, 1383-1386;
31. b) R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez- Gutiérrez, F. Rodríguez, Adv. Synth. Catal. 2006, 348, 1841-1845;
32. c) R. Sanz, D. Miguel, A. Martínez, J. M. Álvarez- Gutiérrez, F. Rodríguez, Org. Lett. 2007, 9, 727-730;
33. d) R. Sanz, D. Miguel, A. Martínez, J. M. Álvarez- Gutiérrez, F. Rodríguez, Org. Lett. 2007, 9, 2027-2030;
34. e) R. Sanz, A. Martínez, V. Guilarte, J. M. Álvarez- Gutiérrez, F. Rodríguez, Eur. J. Org. Chem. 2007, 4642-4645;
35. f) R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez- Gutiérrez, F. Rodríguez, Synthesis 2007, 3252-3256.
36. R. Sanz, D. Miguel, J. M. Álvarez-Gutiérrez, F. Rodríguez, Synlett 2008, 975-978.
37. R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1996.
38. For interesting examples of gold-catalyzed reactions involving indoles, see: a) L. Zhang, J. Am. Chem. Soc. 2005, 127, 16804-16805;
39. b) C. Ferrer, A. M. Echavarren, Angew. Chem. 2006, 118, 1123-1127;
40. Angew. Chem. Int. Ed. 2006, 45, 1105-1109;
41. c) C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358-1373;
42. d) S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Chem. Eur. J. 2007, 13, 8285-8293;
43. e) G. Zhang, X. Huang, G. Li, L. Zhang, J. Am. Chem. Soc. 2008, 130, 1814-1815.
44. For bis(trifluoromethanesulfonyl)imidate-based gold catalysts, see: N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136;
45. for biphenylphosphine-based gold catalysts, see: C. Nieto-Oberhuber, S. López, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
46. P. de Frémont, N. M. Scott, E. D. Stevens, S. P. Nolan, Organometallics 2005, 24, 2411-2418.
47. N. Marion, S. Díez-González, P. de Frémont, A. R. Noble, S. P. Nolan, Angew. Chem. 2006, 118, 3729-3732;
48. Angew. Chem. Int. Ed. 2006, 45, 3647-3650.
49. a) K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505-8513;
50. b) B. A. Bhanu Prasad, F. K. Yoshimoto, R. Sarpong, J. Am. Chem. Soc. 2005, 127, 12468-12469.
51. CCDC 689754 (2c), 689755 (2e), 689756 (12a), and 689757 (12b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
52. For excellent accounts on concurrent tandem catalysis, see: a) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020;
53. b) A. M. Walji, D. W. C. MacMillan, Synlett 2007, 1477-1489.
54. For gold-catalyzed tandem reactions involving an initial [3,3] rearrangement followed by a Nazarov-type cyclization, see: a) L. Zhang, S. Wang, J. Am. Chem. Soc. 2006, 128, 1442-1443;
55. b) G. Lemière, V. Gandon, K. Cariou, T. Fukuyama, A.-L. Dhimane, L. Fensterbank, M. Malacria, Org. Lett. 2007, 9, 2207-2209;
56. c) F.-Q. Shi, X. Li, Y. Xia, L. Zhang, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 15503-15512;
57. for a platinum-catalyzed tandem reaction involving an initial 6-exo-dig cyclization reaction followed by a Nazarov-type cyclization, see: d) S. M. A. Sohel, S.-H. Lin, R.-S. Liu, Synlett 2008, 745-750.
58. a) I.-M. Karaguni, K.-H. Glüsenkamp, A. Langerak, C. Geisen, V. Ullrich, G. Winde, T. Möröy, O. Müller, Bioorg. Med. Chem. Lett. 2002, 12, 709-713;
59. b) A. Kort, J. Legros, C. Bolm, Synlett 2004, 2397-2399.