Halogenation of 1,1-diaryl alkenes

Tetrahedron Letters

Volumn 52, Issue 7, 2011, Pages 826-829

  Chang, Meng Yang ^a   Lee, Ming Fang ^a   Lin, Chung Han ^a   Lee, Nein Chia ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

1,1 Diaryl alkenes; N Halosuccinimide; Vinyl halides

Indexed keywords

1,1 DIARYL ALKENE; ALKENE DERIVATIVE; BASE; HALIDE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; HALOGENATION; SYNTHESIS;

EID: 78651396308     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.12.041     Document Type: Article

References (53)

1. For vinyl fluorides: J.H. van Steenis, and A. van der Gen J. Chem. Soc., Perkin Trans. 1 2002 2117 and references cited herein
2. Y. Shen J. Organomet. Chem. 691 2006 1452
3. For vinyl chlorides, bromides: W. Li, J. Li, Z.-K. Wan, J. Wu, and W. Massefski Org. Lett. 9 2007 4607 and references cited herein
4. C. Ye, and J.M. Shreeve J. Org. Chem. 69 2004 8561
5. For vinyl selenides: G. Perin, E.J. Lenardao, R.G. Jacob, and R.B. Panatieri Chem. Rev. 109 2009 1277
6. G. Grossma, M. Poncioni, M. Bornand, B. Jolivet, M. Neuburger, and U. Sequin Tetrahedron 59 2003 3237
7. J. Thibonnet, V.A. Vu, L. Berillon, and P. Knochel Tetrahedron 58 2002 4787
8. I. Pravst, M. Zupan, and S. Stavber Curr. Org. Chem. 13 2009 47
9. M.-Y. Chang, R.-T. Hsu, T.-W. Tseng, P.-P. Sun, and N.C. Chang Tetrahedron 60 2004 5545
10. P.-P. Sun, M.-Y. Chang, M.-Y. Chiang, and N.-C. Chang Org. Lett. 5 2003 1761
11. H. Gutke, N.A. Braun, and D. Spitzner Tetrahedron 60 2004 8137
12. E. Bellur, and P. Langer Eur. J. Org. Chem. 2005 4815
13. H. Veisi, and R. Ghorbani-Vaghei Tetrahedron 66 2010 7445
14. R.J. Sciotti, M. Pliushchev, P.E. Wiedeman, D. Balli, R. Flamm, A.M. Nilius, K. Marsh, D. Stolarik, R. Jolly, R. Ulrich, and S.W. Djuric Bioorg. Med. Chem. Lett. 12 2002 2121
15. S.-Y. Han, H. Inoue, T. Terada, S. Kamoda, Y. Saburi, K. Sekimata, T. Saito, M. Kobayashi, K. Shinozaki, S. Yoshida, and T. Asami Bioorg. Med. Chem. Lett. 12 2002 1139
16. R. Bohlmann J. Fluorine Chem. 58 1992 192
17. N. Asakura, Y. Usuki, H. Iio, and T. Tanaka J. Fluorine Chem. 127 2006 808
18. B. Yin, L. Wang, S. Inagi, and T. Fuchigami Tetrahedron 66 2010 6820
19. M.D. Crenshaw, and H. Zimmer J. Med. Chem. 48 1983 2782
20. R.T. Turner, G.L. Evans, J.P. Sluka, M.D. Adrian, H.U. Bryant, C.H. Turner, and M. Sato Endocrinology 139 1998 3712
21. W. Sneader Drug Discovery 2005 255
22. R. Romagnoli, P.G. Baraldi, M.A. Tabrizi, J. Bermejo, F. Estevez, M. Borgatti, and R. Gambari J. Med. Chem. 48 2005 7906
23. I. Beria, P.G. Baraldi, P. Cozzi, M. Caldarelli, C. Geroni, S. Marchini, N. Mongelli, and R. Romagnoli J. Med. Chem. 47 2004 2611
24. D.P. Mattews, P.P. Waid, J.S. Sabol, and J.R. McCarthy Tetrahedron Lett. 35 1994 5177
25. M. Marhold, A. Buer, H. Hiemstra, J.H. van Maarseveen, and G. Haufe Tetrahedron Lett. 45 2004 57
26. J.R. McCarthy, D.P. Matthews, M.L. Edwards, D.M. Stemerick, and E.T. Jarvi Tetrahedron Lett. 31 1990 5449
27. D.M. Hodgson, and T. Arif J. Am. Chem. Soc. 130 2008 16500
28. L.X. Shao, and M. Shi Synlett 2006 1269
29. Y. Wang, and H.W. Lam J. Org. Chem. 74 2009 1353
30. H.-X. Wei, R.L. Jasoni, J. Hu, G. Li, and P.W. Pare Tetrahedron 60 2004 10233
31. W. Li, J. Li, Z.-K. Wan, J. Wu, and W. Massefski Org. Lett. 9 2007 4607
32. S. Stavber, T. Sotler-Pecan, and M. Zupan Tetrahedron 50 1994 12235
33. S. Stavber, T. Sotler-Pecan, and M. Zupan Bull. Chem. Soc. Jpn. 69 1996 169
34. S. Stavber, M. Zupan, A.J. Poss, and G.A. Shia Tetrahedron Lett. 36 1995 6769
35. P.T. Nyffeler, S.G. Duron, M.D. Burkart, S.P. Vincent, and C.H. Wong Angew. Chem., Int. Ed. 44 2005 192
36. S. France, A. Weatherwax, and T. Lectka Eur. J. Org. Chem. 2005 475
37. R.P. Singh, and J.M. Shreeve Acc. Chem. Res. 37 2004 31
38. J.-A. Ma, and D. Cahard Chem. Rev. 104 2004 6119
39. R.E. Banks J. Fluorine Chem. 87 1998 1
40. M. Shimizu, and T. Hiyama Angew. Chem., Int. Ed. 44 2005 214
41. P.M. Pihko Angew. Chem., Int. Ed. 45 2006 544
42. K. Uneyama Organofluorine Chemistry 1st ed. 2006 Blackwell Publishing Ltd Oxford
43. C.C. Silveira, A.L. Braga, T.S. Kaufman, and E.J. Lenardao Tetrahedron 60 2004 8295
44. B.L. Jensen, and S.V. Slobodzian Tetrahedron Lett. 41 2000 6029
45. N.J. Alcock, I. Mann, P. Peach, and M. Wills Tetrahedron: Asymmetry 13 2002 2485
46. D.E. Nichols, J.M. Cassady, P.E. Persons, M.C. Yeung, and J.A. Clemens J. Med. Chem. 32 1989 2128
47. 2: C, 76.04; H, 6.03. Found: C, 76.43; H, 6.32.
48. CCDC 784042 (2a), 789504 (2c), 789886 (2f), 776260 (2g), 790221 (2h), and 789691 (2m) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk ).
49. M.-Y. Chang, T.-C. Wu, C.-Y. Lin, and C.-Y. Hung Tetrahedron Lett. 47 2006 8347
50. J.B. Rhoden, M. Bouvet, S. Izenwasser, D. Wade, S.A. Lomenzo, and M.L. Trudell Bioorg. Med. Chem. 13 2005 5623
51. C.W. Lindsley, Z. Zhao, W.H. Leister, J. O'Brien, W. Lemaire, D.L. Williams Jr., T.-B. Chen, R.S.L. Chang, M. Burno, M.A. Jacobson, C. Sur, G.G. Kinney, D.J. Pettibone, P.R. Tiller, S. Smith, N.N. Tsou, M.E. Duggan, P.J. Conn, and G.D. Hartman ChemMedChem 1 2006 807
52. M.-Y. Chang, C.-H. Lin, Y.-L. Chen, R.-T. Hsu, and C.-Y. Chang Tetrahedron Lett. 51 2010 3154
53. CCDC 789892 (8a), 772680 (9), and 772681 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: 44-1223-336033; e-mail: http://deposit@ccdc. cam.ac.uk ).