Facile synthesis of 2-bromoindoles by ligand-free CuI-catalyzed intramolecular cross-coupling of gem-dibromoolefins

Tetrahedron Letters

Volumn 51, Issue 48, 2010, Pages 6342-6344

  Jiang, Baishan ^a   Tao, Kemei ^a   Shen, Wang ^c   Zhang, Jiancun ^a,b  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

^b GUANGZHOU MEDICAL UNIVERSITY   (China)

^c Kanion USA Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOINDOLE; ALKENE DERIVATIVE; COPPER ION; INDOLE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; HALOGENATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 78049406981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.129     Document Type: Article

References (48)

1. For selected papers, see: W. Shi, R.S. Coleman, and T.L. Lowary Org. Biomol. Chem. 7 2009 3709
2. T.C. Leboho, J.P. Michael, W.A.L.V. Otterlo, S.F.V. Vuuren, and C.B.D. Koning Bioorg. Med. Chem. Lett. 19 2009 4948
3. R. Pathak, J.M. Nhlapo, S. Govender, J.P. Michael, W.A.L.V. Otterlo, and C.B.D. Koning Tetrahedron 62 2006 2820
4. W. Fröhner, B. Monse, T.M. Braxmeier, L. Casiraghi, H. Sahagun, and P. Seneci Org. Lett. 7 2005 4573
5. S. Harper, S. Avolio, B. Pacini, M.D. Filippo, and S. Altamura J. Med. Chem. 48 2005 4547
6. S. Roya, and G.W. Gribble Tetrahedron Lett. 46 2005 1325
7. M.W. Hooper, M. Utsunomiya, and J.F. Hartwig J. Org. Chem. 68 2003 2861
8. For selected papers, see: V.J. Klimkowski, B.M. Watson, M.R. Wiley, J. Liebeschuetz, J.B. Franciskovich, and S.M. Sheehan Bioorg. Med. Chem. Lett. 17 2007 5801
9. J.X. Qiao, C.-H. Chang, D.L. Cheney, P.E. Morin, G.Z. Wang, and S.R. King Bioorg. Med. Chem. Lett. 19 2007 4419
10. A. Andreani, S. Burnelli, M. Granaiola, A. Leoni, A. Locatelli, and R. Morigi J. Med. Chem. 50 2007 3167
11. For representative papers on the synthesis of 2- or 3-halogenated indoles, see: S. Tang, J.-H. Li, Y.-X. Xie, and N.-X. Wang Synthesis 2007 1535
12. A. Fiumana, and K. Jones Tetrahedron Lett. 41 2000 4209
13. R. Liu, P. Zhang, T. Gan, and J.M. Cook J. Org. Chem. 62 1997 7447
14. P. Zhang, R. Liu, and J.M. Cook Tetrahedron Lett. 36 1995 3103
15. J. Bergman, and L. Venemalm J. Org. Chem. 57 1992 2495
16. A.G. Mistry, K. Smith, and M.R. Bye Tetrahedron Lett. 27 1986 1051
17. É. Balogh-Hergovich, and G. Speier J. Chem. Soc., Perkin Trans. 1 1986 2305
18. V. Bocchi, and G. Palla Synthesis 1982 1096
19. K. Akinori, and N. Tatsuya Synthesis 1980 365
20. For selected papers, see: A. Coste, G. Karthikeyan, F. Couty, and G. Evano Angew. Chem., Int. Ed. 48 2009 4381
21. A. Coste, F. Couty, and G. Evano Org. Lett. 11 2009 4454
22. S.G. Newman, V. Aureggi, C.S. Bryan, and M. Lautens Chem. Commun. 2009 5236
23. W. Ye, J. Mo, T. Zhao, and B. Xu Chem. Commun. 2009 3246
24. D.I. Chai, and M. Lautens J. Org. Chem. 74 2009 3054
25. C.S. Bryan, and M. Lautens Org. Lett. 10 2008 4633
26. Y.-Q. Fang, and M. Lautens J. Org. Chem. 73 2008 538
27. M. Nagamochi, Y.-Q. Fang, and M. Lautens Org. Lett. 9 2007 2955
28. Y.-Q. Fang, Y. Yuen, and M. Lautens J. Org. Chem. 72 2007 5152
29. Y.-Q. Fang, R. Karisch, and M. Lautens J. Org. Chem. 72 2007 1341
30. A. Fayol, Y.-Q. Fang, and M. Lautens Org. Lett. 8 2006 4203
31. J. Yuen, Y.-Q. Fang, and M. Lautens Org. Lett. 8 2006 653
32. Y.-Q. Fang, and M. Lautens Org. Lett. 7 2005 3549
33. S. Thiegles, E. Meddah, P. Bisseret, and J. Eustache Tetrahedron Lett. 45 2004 907
34. A.M. Zhang, X.L. Zheng, J.F. Fan, and W. Shen Tetrahedron Lett. 51 2010 828
35. K. Tao, J. Zheng, Z. Liu, W. Shen, and J. Zhang Tetrahedron Lett. 51 2010 3246
36. W. Shen, T. Kohn, Z. Fu, X.-Y. Jiao, S. Lai, and M. Schmitt Tetrahedron Lett. 49 2008 7284
37. W. Shen, and A. Kunzer Org. Lett. 4 2002 1315
38. W. Shen, and S.A. Thomas Org. Lett. 2 2000 2857
39. W. Shen Synlett 2000 737
40. W. Shen, and L. Wang J. Org. Chem. 64 1999 8873
41. L. Wang, and W. Shen Tetrahedron Lett. 39 1998 7625
42. While this manuscript was being prepared, a related formation of 2-bromoindole was published on-line: Z.-J. Wang, J.-G. Yang, F. Yang, and W. Bao Org. Lett. 12 2010 3034
43. +): 355.8779; found: 355.8781.
44. +): 273.9537; found: 273.9533.
45. I.J.S. Fairlamb Chem. Soc. Rev. 36 2007 1036
46. S.T. Handy, and Y.N. Zhang Chem. Commun. 2006 299
47. X. Liu, H. Fu, Y. Jiang, and Y. Zhao Angew. Chem., Int. Ed. 48 2009 348
48. Q. Cai, B. Zou, and D. Ma Angew. Chem., Int. Ed. 45 2006 1276