5-endo-Trigonal cyclization of o-substituted gem-difluorostyrenes: Syntheses of 2-fluorinated indoles, benzo[b]furans and benzo[b]thiophenes

Chemical Communications

Volumn , Issue 16, 1997, Pages 1537-1538

  Ichikawa, Junji ^a   Wada, Yukinori ^a   Okauchi, Tatsuo ^a   Minami, Toru ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000256371     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703110f     Document Type: Article

References (40)

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18. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; Y. Landais and D. Planchenault, Synlett, 1995, 1191 and references cited therein; B. H. Lipshutz and T. Gross, J. Org. Chem., 1995, 60, 3572 and references cited therein; M. Kimura, H. Harayama, S. Tanaka and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.
19. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; Y. Landais and D. Planchenault, Synlett, 1995, 1191 and references cited therein; B. H. Lipshutz and T. Gross, J. Org. Chem., 1995, 60, 3572 and references cited therein; M. Kimura, H. Harayama, S. Tanaka and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.
20. A. D. Jones and D. W. Knight, Chem. Commun., 1996, 915; Y. Landais and D. Planchenault, Synlett, 1995, 1191 and references cited therein; B. H. Lipshutz and T. Gross, J. Org. Chem., 1995, 60, 3572 and references cited therein; M. Kimura, H. Harayama, S. Tanaka and Y. Tamaru, J. Chem. Soc., Chem. Commun., 1994, 2531.
21. For 5-endo radical cyclizations onto an unsaturated carbon, see T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908; T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; A. V. R. Rao, A. K. Singh, K. M. Reddy and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1993, 3171. See, also: D. L. J. Clive and W. Yang, Chem. Commun., 1996, 1605. For 5-endo radical cyclizations onto a multiple-bonded, first-row heteroatom, see: Y. Yamamoto, M. Ohno and S. Eguchi, J. Org. Chem., 1996, 61, 9264 and references cited therein.
22. For 5-endo radical cyclizations onto an unsaturated carbon, see T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908; T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; A. V. R. Rao, A. K. Singh, K. M. Reddy and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1993, 3171. See, also: D. L. J. Clive and W. Yang, Chem. Commun., 1996, 1605. For 5-endo radical cyclizations onto a multiple-bonded, first-row heteroatom, see: Y. Yamamoto, M. Ohno and S. Eguchi, J. Org. Chem., 1996, 61, 9264 and references cited therein.
23. For 5-endo radical cyclizations onto an unsaturated carbon, see T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908; T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; A. V. R. Rao, A. K. Singh, K. M. Reddy and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1993, 3171. See, also: D. L. J. Clive and W. Yang, Chem. Commun., 1996, 1605. For 5-endo radical cyclizations onto a multiple-bonded, first-row heteroatom, see: Y. Yamamoto, M. Ohno and S. Eguchi, J. Org. Chem., 1996, 61, 9264 and references cited therein.
24. For 5-endo radical cyclizations onto an unsaturated carbon, see T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908; T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; A. V. R. Rao, A. K. Singh, K. M. Reddy and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1993, 3171. See, also: D. L. J. Clive and W. Yang, Chem. Commun., 1996, 1605. For 5-endo radical cyclizations onto a multiple-bonded, first-row heteroatom, see: Y. Yamamoto, M. Ohno and S. Eguchi, J. Org. Chem., 1996, 61, 9264 and references cited therein.
25. For 5-endo radical cyclizations onto an unsaturated carbon, see T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908; T. Sato, N. Chono, H. Ishibashi and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 1995, 1115; A. V. R. Rao, A. K. Singh, K. M. Reddy and K. Ravikumar, J. Chem. Soc., Perkin Trans. 1, 1993, 3171. See, also: D. L. J. Clive and W. Yang, Chem. Commun., 1996, 1605. For 5-endo radical cyclizations onto a multiple-bonded, first-row heteroatom, see: Y. Yamamoto, M. Ohno and S. Eguchi, J. Org. Chem., 1996, 61, 9264 and references cited therein.
26. M. J. Silvester, Adv. Heterocycl. Chem., 1994, 59, 1; Aldrichim. Acta, 1991, 24, 31; Organofluorine Chemistry, Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York, 1994.
27. M. J. Silvester, Adv. Heterocycl. Chem., 1994, 59, 1; Aldrichim. Acta, 1991, 24, 31; Organofluorine Chemistry, Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York, 1994.
28. M. J. Silvester, Adv. Heterocycl. Chem., 1994, 59, 1; Aldrichim. Acta, 1991, 24, 31; Organofluorine Chemistry, Principles and Commercial Applications, ed. R. E. Banks, B. E. Smart and J. C. Tatlow, Plenum Press, New York, 1994.
29. J. Jenikoba, T. Minami, T. Sonoda and H. Kobayashi, Tetrahedron Lett., 1992, 33, 3779; see also: J. Ichikawa, M. Fujiwara, H. Nawata, T. Ukauchi and T. Minami, Tetrahedron Lett., 1996, 37, 8799.
30. J. Jenikoba, T. Minami, T. Sonoda and H. Kobayashi, Tetrahedron Lett., 1992, 33, 3779; see also: J. Ichikawa, M. Fujiwara, H. Nawata, T. Ukauchi and T. Minami, Tetrahedron Lett., 1996, 37, 8799.
31. For the synthesis of fluoroindoles, see H. F. Hodson, D. J. Madge, A. N. Z. Slawin, D. A. Widdowson and D. J. Williams, Tetrahedron, 1994, 50, 1899. For the synthesis of fluoropyrroles, see Z.-M. Qiu and D. J. Burton, Tetrahedron Lett., 1995, 36, 5119; J. Leroy and C. Wakselman, Tetrahedron Lett., 1994, 35, 8605 and references cited therein.
32. For the synthesis of fluoroindoles, see H. F. Hodson, D. J. Madge, A. N. Z. Slawin, D. A. Widdowson and D. J. Williams, Tetrahedron, 1994, 50, 1899. For the synthesis of fluoropyrroles, see Z.-M. Qiu and D. J. Burton, Tetrahedron Lett., 1995, 36, 5119; J. Leroy and C. Wakselman, Tetrahedron Lett., 1994, 35, 8605 and references cited therein.
33. For the synthesis of fluoroindoles, see H. F. Hodson, D. J. Madge, A. N. Z. Slawin, D. A. Widdowson and D. J. Williams, Tetrahedron, 1994, 50, 1899. For the synthesis of fluoropyrroles, see Z.-M. Qiu and D. J. Burton, Tetrahedron Lett., 1995, 36, 5119; J. Leroy and C. Wakselman, Tetrahedron Lett., 1994, 35, 8605 and references cited therein.
34. For the synthesis of fluorobenzo[b]furans, see: D. H. R. Barton, R. H. Hesse, G. P. Jackman and M. M. Pechet, J. Chem. Soc., Perkin Trans. 1, 1977, 2604. For the synthesis of fluorofurans, see A. K. Forrest and P. J. O'Hanlon, Tetrahedron Lett., 1995, 36, 2117; K. Burger and B. Helmreich, J. Chem. Soc., Chem. Commun., 1992, 348; H. L. Sham and D. A. Betebenner, J. Chem. Soc., Chem. Commun., 1991, 1134.
35. For the synthesis of fluorobenzo[b]furans, see: D. H. R. Barton, R. H. Hesse, G. P. Jackman and M. M. Pechet, J. Chem. Soc., Perkin Trans. 1, 1977, 2604. For the synthesis of fluorofurans, see A. K. Forrest and P. J. O'Hanlon, Tetrahedron Lett., 1995, 36, 2117; K. Burger and B. Helmreich, J. Chem. Soc., Chem. Commun., 1992, 348; H. L. Sham and D. A. Betebenner, J. Chem. Soc., Chem. Commun., 1991, 1134.
36. For the synthesis of fluorobenzo[b]furans, see: D. H. R. Barton, R. H. Hesse, G. P. Jackman and M. M. Pechet, J. Chem. Soc., Perkin Trans. 1, 1977, 2604. For the synthesis of fluorofurans, see A. K. Forrest and P. J. O'Hanlon, Tetrahedron Lett., 1995, 36, 2117; K. Burger and B. Helmreich, J. Chem. Soc., Chem. Commun., 1992, 348; H. L. Sham and D. A. Betebenner, J. Chem. Soc., Chem. Commun., 1991, 1134.
37. For the synthesis of fluorobenzo[b]furans, see: D. H. R. Barton, R. H. Hesse, G. P. Jackman and M. M. Pechet, J. Chem. Soc., Perkin Trans. 1, 1977, 2604. For the synthesis of fluorofurans, see A. K. Forrest and P. J. O'Hanlon, Tetrahedron Lett., 1995, 36, 2117; K. Burger and B. Helmreich, J. Chem. Soc., Chem. Commun., 1992, 348; H. L. Sham and D. A. Betebenner, J. Chem. Soc., Chem. Commun., 1991, 1134.
38. R. N. Young, J. Y. Gauthier and W. Coombs, Tetrahedron Lett., 1984, 25, 1753.
39. For the synthesis of fluorobenzo[b]thiophenes, see; P. Nussbaumer, G. Petrenyi and A. Stütz, J. Med. Chem., 1991, 34, 65. For the synthesis of fluorothiophenes, see K. Burger and B. Helmreich, Heterocycles, 1994, 39, 819.
40. For the synthesis of fluorobenzo[b]thiophenes, see; P. Nussbaumer, G. Petrenyi and A. Stütz, J. Med. Chem., 1991, 34, 65. For the synthesis of fluorothiophenes, see K. Burger and B. Helmreich, Heterocycles, 1994, 39, 819.