From PtCl2- and acid-catalyzed to uncatalyzed cycloisomerization of 2-propargyl anilines: Access to functionalized indoles

Angewandte Chemie - International Edition

Volumn 46, Issue 11, 2007, Pages 1881-1884

  Cariou, Kevin ^a   Ronan, Baptiste ^b   Mignani, Serge ^b   Fensterbank, Louis ^a   Malacria, Max ^a  

^a CNRS   (France)

^b Centre de Recherche de Paris   (France)

Author keywords

Cycloisomerization; Fused ring systems; Indoles; Platinum; Synthetic methods

Indexed keywords

ACTIVATION ENERGY; ANILINE; AROMATIC COMPOUNDS; CATALYSIS; ISOMERIZATION; SUBSTITUTION REACTIONS;

CYCLOISOMERIZATION; FUSED-RING SYSTEMS; INDOLES; SYNTHETIC METHODS;

PLATINUM COMPOUNDS;

ANILINE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GOLD; INDOLE DERIVATIVE; METAL; PLATINUM CHLORIDE; PLATINUM DERIVATIVE; PROTON; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; ISOMERISM; PROTEIN PROCESSING; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; CYCLIZATION; GOLD; INDICATORS AND REAGENTS; INDOLES; ISOMERISM; METALS; PLATINUM COMPOUNDS; PROTEIN ISOPRENYLATION; PROTONS; TRIMETHYLSILYL COMPOUNDS;

EID: 34249686688     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604026     Document Type: Article

References (63)

1. For recent reviews on the synthesis of indoles, see a) A. R. Katritzky, A. F. Pozharskii, Handbook of Heterocyclic Chemistry, Pergamon, Oxford, 2000, chap. 4;
2. b) G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075;
3. c) J. A. Joule in Science of Synthesis, Vol. 10 (Ed.: E. J. Thomas), Georg Thieme, Stuttgart, 2000, pp. 361-652.
4. For palladium catalysis, see a) S. Cacchi, G. Fabrizi, P. Pace, J. Org. Chem. 1998, 63, 1001-1011;
5. b) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, L. M. Parisi, J. Org. Chem. 2005, 70, 6213-6217;
6. for reviews see: c) S. Cacchi, J. Organomet. Chem. 1999, 576, 42-64;
7. d) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
8. e) S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920;
9. f) M. Lautens, D. Alberico, C. Bressy, Pure Appl. Chem. 2006, 78, 351-361.
10. II-catalyzed 5-endo-dig approach to indoles and benzofuranes, see a) A. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15 024-15 025;
11. b) I. Nakamura, Y. Mizushima, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 15 022-15 023;
12. for gold-catalyzed related transformations, see c) M. Alfonsi, A. Arcadi, M. Aschi, G. Bianchi, F. Marinelli, J. Org. Chem. 2005, 70, 2265-2273;
13. d) R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555-4563;
14. e) N. Morita, N. Krause, Eur. J. Org. Chem. 2006, 4634-4641;
15. f) S. K. Hashmi, M. Rudolph, S. Schymura, J. Visus, W. Frey, Eur. J. Org. Chem. 2006, 4905-4909;
16. g) G. Abbiati, A. Arcadi, E. Beccalli, G. Bianchi, F. Marinelli, E. Rossi, Tetrahedron 2006, 62, 3033-3039, and references therein.
17. II catalysts, see H. Kusama, Y. Miyashita, J. Takaya, N. Iwasawa, Org. Lett. 2006, 8, 289-292.
18. For 5-exo-trig palladium-catalyzed strategies, see a) L. S. Hegedus, G. F. Allen, J. J. Bozell, E. L. Waterman, J. Am. Chem. Soc. 1978, 100, 5800-5807;
19. b) M. Gowan, A. S. Caillé, C. K. Lau, Synlett 1997, 1312-1314.
20. a) N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104-9105;
21. b) A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11 863-11 869;
22. c) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2001, 123, 10 511-10 520;
23. d) C. Nevado, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2003, 9, 2627-2635;
24. e) W. D. Kerber, J. H. Koh, M. R. Gagné, Org. Lett. 2004, 6, 3013-3015;
25. for reviews, see f) M. Méndez, V. Mamane, A. Fürstner, Chemtracts: Org. Chem. 2003, 16, 397-425;
26. g) G. C. Lloyd-Jones, Org. Biomol. Chem. 2003, 1, 215-236;
27. h) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
28. i) L. Añorbe, G. Domínguez, J. Pérez-Castells, Chem. Eur. J. 2004, 10, 4938-4943;
29. j) S. T. Diver, A. J. Giessert, Chem. Rev. 2004, 104, 1317-1382;
30. k) A. M. Echavarren, C. Nevado, Chem. Soc. Rev. 2004, 33, 431-436.
31. a) B. M. Trost, G. A. Doherty, J. Am. Chem. Soc. 2000, 122, 3801-3810;
32. b) A. Fürstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 1998, 120, 8305-8314.
33. a) L. Charruault, V. Michelet, R. Taras, S. Gladiali, J.-P. Genêt, Chem. Commun. 2004, 850-851;
34. b) C. Liu, X. Han, X. Wang, R. A. Wiedenhoefer, J. Am. Chem. Soc. 2004, 126, 3700-3701.
35. a) N. Cadran, K. Cariou, G. Hervé, C. Aubert, L. Fensterbank, M. Malacria, J. Marco-Contelles, J. Am. Chem. Soc. 2004, 126, 3408-3409;
36. b) F. Marion, J. Coulomb, C. Courillon, L. Fensterbank, M. Malacria, Org. Lett. 2004, 6, 1509-1511.
37. a) E. Mainetti, V. Mouriès, L. Fensterbank, M. Malacria, J. Marco-Contelles, Angew. Chem. 2002, 114, 2236-2239;
38. Angew. Chem. Int. Ed. 2002, 41, 2132-2135;
39. b) Y. Harrak, C. Blaszykowski, M. Bernard, K. Cariou, E. Mainetti, V. Mouriès, A.-L. Dhimane, L. Fensterbank, M. Malacria, J. Am. Chem. Soc. 2004, 126, 8656-8657;
40. c) J. Marco-Contelles, N. Arroyo, S. Anjum, E. Mainetti, N. Marion, K. Cariou, G. Lemière, V. Mouriès, L. Fensterbank, M. Malacria, Eur. J. Org. Chem. 2006, 4618-4633.
41. For related starting materials, see a) M. Gray, P. J. Parsons, A. P. Neary, Synlett 1993, 281-282;
42. b) B. Gabriele, R. Mancuso, G. Salerno, L. Veltri, Chem. Commun. 2005, 271-273;
43. c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai, S. Uemura, J. Am. Chem. Soc. 2004, 126, 16 066-16 072;
44. d) N. Höenke, L. J. Payne, P. J. Parsons, P. B. Hitchcock, Synlett 2006, 654-656.
45. For a 5-exo-dig iodo-catalyzed strategy, see K. O. Hessian, B. L. Flynn, Org. Lett. 2006, 8, 243-246.
46. Enyne metathesis has also been shown to be catalyzed by Brønsted and Lewis acids, see Ref. [6b]; see also a) Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B. W. Slafer, A. Davis, Org. Lett. 2005, 7, 1047-1050;
47. b) L. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2004, 126, 10 204-10 205.
48. a) G. R. Cook, J. R. Stille, J. Org. Chem. 1991, 56, 5578-5583;
49. b) D. F. McComsey, B. E. Maryanoff, J. Org. Chem. 2000, 65, 4938-4943;
50. c) U. Nubbemeyer, Top. Curr. Chem. 2006, 244, 149-213.
51. a) V. Rautenstrauch, J. Org. Chem. 1984, 49, 950-952;
52. b) K. Cariou, E. Mainetti, L. Fensterbank, M. Malacria, Tetrahedron 2004, 60, 9745-9755;
53. c) V. Mamane, T. Gress, H. Krause, A. Fürstner, J. Am. Chem. Soc. 2004, 126, 8654-8655;
54. d) K. Miki, K. Ohe, S. Uemura J. Org. Chem. 2003, 68, 8505-8513;
55. e) C. Fehr, J. Galindo, Angew. Chem. 2006, 118, 2967-2970;
56. Angew. Chem. Int. Ed. 2006, 45, 2901-2904.
57. P. González-Pérez, L. Pérez-Serrano, L. Casarrubios, G. Domínguez, J. Pérez-Castells, Tetrahedron Lett. 2002, 43, 4765-4767.
58. The structure of 5a was confirmed by X-ray analysis of the analogous para-nitrobenzoate ester. CCDC-626845 contains 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.
59. a) E. Desarbre, L. Savelon, O. Cornec, J. Y. Mérour, Tetrahedron 1996, 52, 2983-2994;
60. b) O. R. Suárez-Castillo, M. Sánchez-Zavala, M. Meléndez-Rodríguez, L. E. Castel-Duarte, M. S. Morales-Ríos, P. Joseph-Nathan, Tetrahedron 2006, 62, 3040-3051.
61. S. Kafka, A. Klásek, J. Kosmrlj, J. Org. Chem. 2001, 66, 6394-6399.
62. The structure of 8 was confirmed by X-ray analysis of the N-benzyl derivative. CCDC-626846 contains 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.
63. T. Kawasaki, M. Nagaoka, T. Satoh, A. Okamoto, R. Ukon, A. Ogawa, Tetrahedron 2004, 60, 3493-3503.