Palladium-catalyzed aryl amination-heck cyclization cascade: A one-flask approach to 3-substituted indoles

Angewandte Chemie - International Edition

Volumn 47, Issue 5, 2008, Pages 888-890

  Jensen, Thomas ^b   Pedersen, Henrik ^a   Bang Andersen, Benny ^a   Madsen, Robert ^b   Jørgensen, Morten ^a  

^a H LUNDBECK A S   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Amination; Heck reaction; Indoles; Palladium; Phosphane ligands

Indexed keywords

AMINES; AROMATIC COMPOUNDS; CYCLIZATION; ISOMERS; LIGANDS; PALLADIUM COMPOUNDS;

ALLYLIC AMINES; HECK REACTION; REGIOISOMERS;

AMINATION;

INDOLE DERIVATIVE; LIGAND; ORGANOMETALLIC COMPOUND; PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINATION; CATALYSIS; CYCLIZATION; INDOLES; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 38549087936     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200703763     Document Type: Article

References (41)

1. For an overview, see: K. P. Bøgesø, B. Bang-Andersen in Textbook of Drug Design and Discovery, 3rd ed. (Eds.: P. Krogsgaard-Larsen, T. Liljefors, U. Madsen), Taylor and Francis, London, UK, 2002, chap. 11.
2. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875.
3. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873.
4. N. V. Kondratenko, A. A. Kolomeitsev, V. O. Mogilevskaya, N. M. Varlamova, L. M. Yagupol'skii, J. Org. Chem. USSR 1986, 22, 1571 (article published in Russian in 1985).
5. a) J. Louie, J. F. Hartwig, Tetrahedron Lett. 1995, 36, 3609;
6. b) A. S. Guram, R. A. Rennels, S. L. Buchwald, Angew. Chem. 1995, 107, 1456;
7. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348;
8. see also: B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599.
9. a) S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 6621;
10. b) S. Wagaw, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 10251.
11. a) L. Ackermann, Org. Lett. 2005, 7, 439;
12. b) L. T. Kaspar, L. Ackermann, Tetrahedron 2005, 61, 11311;
13. c) L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652;
14. Angew. Chem. Int. Ed. 2007, 46, 1627;
15. see also: L. Ackermann, Synlett 2007, 507.
16. S. D. Edmondson, A. Mastracchio, E. R. Parmee, Org. Lett. 2000, 2, 1109.
17. K. Yamazaki, Y. Nakamura, Y. Kondo, J. Chem. Soc. Perkin Trans. 1 2002, 2137.
18. T. Dahl, C. W. Tornøe, B. Bang-Andersen, P. Nielsen, M. Jørgensen, H. Lundbeck, unpublished results.
19. a) R. Odle, B. Blevins, M. Ratcliff, L. S. Hegedus, J. Org. Chem. 1980, 45, 2709;
20. b) L. S. Hegedus, G. F. Allen, J. J. Bozell, E. L. Waterman, J. Am. Chem. Soc. 1978, 100, 5800.
21. M. O. Terpko, R. F. Heck, J. Am. Chem. Soc. 1979, 101, 5281.
22. M. Mori, K. Chiba, Y. Ban, Tetrahedron Lett. 1977, 18, 1037.
23. All chemicals were weighed out in air, and no precautions were taken to exclude air from the reaction mixture. Abbreviations: binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl; davephos = 2-dicyclohexylphosphanyl-2′-(N,N′-dimethylamino)biphenyl; dpephos = bis(2-diphenylphosphanyl)ether; xantphos = 4,5-bis(diphenylphosphanyl) -9,9-dimethylxanthene; x-phos = 2-dicyclohexylphosphanyl-2′,4′, 6′-triisopropyl-1,1′-biphenyl.
24. a) G. Mann, D. Barañano, J. F. Hartwig, A. L. Rheingold, I. A. Guzei, J. Am. Chem. Soc. 1998, 120, 9205;
25. b) M. S. Driver, J. F. Hartwig, J. Am. Chem. Soc. 1997, 119, 8232.
26. For an overview of the Buchwald ligands, see: L. Liang, S. L. Buchwald in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004.
27. Y. Guari, G. P. F. van Strijdonck, M. D. K. Boele, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Chem. Eur. J. 2001, 7, 475.
28. a) J. P. Wolfe, S. Wagaw, S. L. Buchwald, J. Am. Chem. Soc. 1996, 118, 7215;
29. b) J. P. Wolfe, S. L. Buchwald, J. Org. Chem. 2000, 65, 1144.
30. Y. Guari, D. S. van Es, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron Lett. 1999, 40, 3789.
31. a) M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617;
32. b) J. F. Hartwig, M. Kawatsura, S. I. Hauck, K. H. Shaughnessy, L. M. Alcazar-Roman, J. Org. Chem. 1999, 64, 5575;
33. c) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295.
34. W. A. Herrmann, Angew. Chem. 2002, 114, 1342;
35. Angew. Chem. Int. Ed. 2002, 41, 1290.
36. a) R. C. Larock, S. Babu, Tetrahedron Lett. 1987, 28, 5291;
37. b) S. Caddick, W. Kofie, Tetrahedron Lett. 2002, 43, 9347.
38. S. Jaime-Figueroa, Y. Liu, J. M. Muchowski, D. G. Putman, Tetrahedron Lett. 1998, 39, 1313.
39. See the Supporting Information for experimental details.
40. 3] (1.25 mol%) and dppf (5 mol%) were then added, as well as the aryl bromide for N arylation of the indole, and the mixture was stirred at 140°C for an additional 18 h.
41. G. Mann, J. F. Hartwig, M. S. Driver, C. Fernández-Rivas, J. Am. Chem. Soc. 1998, 120, 827.