Intermolecular reactions of indol-2-yl radicals: a new route to 2-substituted indoles

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Andrea Fiumana and Keith Jones


Abstract

The generation of indol-2-yl radicals and their addition to a variety of radical acceptors to prepare 2-substituted indoles is presented.


References

  1. B. Giese, Angew. Chem., Int. Ed. Engl., 1985, 24, 553 CrossRef.
  2. D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions: Concepts, Guidelines and Synthetic Applications, VCH, New York, 1995 Search PubMed.
  3. D. P. Curran, Synthesis, 1988, 417 and 489 CrossRef CAS; D. P. Curran, C. P. Jasperse and T. L. Fevig, Chem. Rev., 1991, 91, 1237 CrossRef CAS; B. Giese, B. Kopping, T. Gögel, J. Dickhaut, G. Thoma, K. J. Kulicke and F. Trach, Org. React., 1996, 48, 301 CAS.
  4. A. Nadin and T. Harrison, Tetrahedron Lett., 1999, 40, 4073 CrossRef; K. Jones and M. L. Escudero-Hernandez, Tetrahedron, 1998, 54, 2275 CrossRef CAS.
  5. B. Giese and J. A. González-Gómez, unpublished work cited in ref. 1.
  6. J. Bergman and L. Venemalm, J. Org. Chem., 1992, 57, 2495 CrossRef CAS.
  7. A. R. Katritzky and K. Akutagava, Tetrahedron Lett., 1985, 26, 5935 CrossRef CAS.
  8. S. S. Labadie and E. Teng, J. Org. Chem., 1994, 59, 4250 CrossRef CAS.
  9. A. P. Dobbs, K. Jones and K. T. Veal, Tetrahedron Lett., 1995, 36, 4857 CrossRef CAS; A. P. Dobbs, K. Jones and K. T. Veal, Tetrahedron, 1998, 54, 2149 CrossRef CAS.
  10. G. E. Keck, E. J. Enholm, J. B. Yates and M. R. Wiley, Tetrahedron, 1985, 41, 4079 CrossRef CAS.
  11. G. Stork and P. M. Sher, J. Am. Chem. Soc., 1986, 108, 303 CrossRef CAS.
  12. G. Stork and P. M. Sher, J. Am. Chem. Soc., 1983, 105, 6765 CrossRef CAS.
  13. C.-C. Yang, H.-T. Chang and J.-M. Fang, J. Org. Chem., 1993, 58, 3100 CrossRef CAS.
  14. E. V. Sadanandan, C. P. Srinivasan and M. Vedachalam, Indian J. Chem., Sect. B, 1993, 32, 481.
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