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DOI: 10.1039/CS9972600157 (Review Article) Reference Section for: Chem. Soc. Rev., 1997, 26, 157-167

Trends in organic electrosynthesis

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James Utley

Abstract

Electrochemistry is a clean and convenient method for the generation on a preparative scale of many reactive intermediates (radical-ions, radicals, carbanions, carbocations, quinodimethanes). This forms the basis of organic electrosynthesis and conditions have been devised for selective and useful chemical conversions. Particularly useful and versatile are carbon-carbon bond forming reactions such as those involving the Kolbe reaction, electrohydrodimerisations and N-acyliminium cations. The in situ electrogeneration and regeneration of redox reagents in non-stoichiometric amounts, and the related redox catalysis, is proving to be an attractive, indirect, electrosynthetic approach. And mechanistic insight into useful preparative reactions is now at an advanced stage.

References

  1. J. Utley, Chem. Ind., 1994, 215 Search PubMed; J. Utley, Organic Electrochemistry, ed. H. Lund and M. M. Baizer, 3rd edn., Marcel Dekker, New York, 1991; Search PubMed; J. Utley, Synthetic Organic Electrochemistry, A. J. Fry, John Wiley, New York, 1989. Search PubMed.
  2. F. Walsh and D. Robinson, Chem. Tech. Eur., 1995, 2, 16 Search PubMed.
  3. L. Eberson and M. Nilsson, J. Chem. Soc., Chem. Commun., 1992, 1041 Search PubMed.
  4. H. J. Schäfer, A. Weiper, M. aus dem Kahmen and A. Matzeit, Perspektiven für die Chemie, VCH, 1993, 97. Search PubMed.
  5. M. Harenbrock, A. Matzeit and H. J. Schäfer, Liebigs Ann., 1996, 55 Search PubMed.
  6. B. C. L. Weedon, Quart. Rev., 1952, 6, 380 Search PubMed; B. C. L. Weedon, Adv. Org. Chem., 1960, 1 Search PubMed.
  7. K. Uneyama, Tetrahedron, 1991, 47, 555 Search PubMed , and earlier refs..
  8. A. Matzeit, H. J. Schafer and C. Amatore, Synthesis, 1995, 1432 Search PubMed.
  9. (a) E. A. Casanova, M. C. Dutton, D. J. Kalota and J. H. Wagenknecht, J. Electrochem. Soc., 1993, 140, 2565 Search PubMed; (b) I. Fussing, M. Gullu, O. Hammerich, A. Hussain, M. F. Nielsen and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1996, 649 Search PubMed; (c) J. H. P. Utley, M. Gullu and M. Motevalli, J. Chem. Soc., Perkin Trans. 1, 1995, 1961 Search PubMed.
  10. D. Degner, Top. Curr. Chem., 1988, 148, 1 Search PubMed.
  11. M. Barl, D. Degner, H. Siegel and W. Hoffmann, DE 2 935 398 (BASF); M. Barl, D. Degner, H. Siegel and W. Hoffmann, Chem. Abstr., 1981, 95, 24556y Search PubMed.
  12. (a) M. Thaning and L. G. Wistrand, J. Org. Chem., 1990, 55, 1406 Search PubMed; (b) U. Slomczynska, D. K. Chalmers, F. Cornille, M. L. Smythe, D. D. Beusen, K. D. Moeller and G. R. Marshall, J. Org. Chem., 1996, 61, 1198 Search PubMed , and earlier refs..
  13. R. D. Little, Chem. Rev., 1996, 96, 93 Search PubMed.
  14. N. G. New, Z. Tesfai and K. D. Moeller, J. Org. Chem., 1996, 61, 1578 Search PubMed , and earlier refs..
  15. Handbook of Conducting Polymers, ed. T. A. Skotheim, Marcel Dekker, New York, 1986. Search PubMed.
  16. J. H. P. Utley, Y. Gao, J. Gruber and R. Lines, J. Mater. Chem., 1995, 5, 1297 Search PubMed.
  17. J. H. P. Utley, Y. Gao, J. Gruber, Y. Zhang and A. Munoz-Escalona, J. Mater. Chem., 1995, 5, 1837 Search PubMed.
  18. A. Papadopoulos, J. Heyer, K. D. Ginzel and E. Steckhan, Chem. Ber., 1989, 122, 2159 Search PubMed; A. Papadopoulos, B. Lewall, E. Steckhan, K. D. Ginzel, F. Knoch and M. Nieger, Tetrahedron, 1991, 47, 563 Search PubMed.
  19. A. Guirado, G. P. Moss and J. H. P. Utley, J. Chem. Soc., Chem. Commun., 1987, 41 Search PubMed.
  20. (a) D. W. Sopher and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1984, 1361 Search PubMed; (b) C. Hackmann and H. J. Schäfer, Tetrahedron, 1993, 49, 4559 Search PubMed.
  21. R. P. Kreh, R. M. Spotnitz and J. T. Lundquist, J. Org. Chem., 1989, 54, 1526 Search PubMed.
  22. T. Fuchigami and T. Fujita, J. Org. Chem., 1994, 59, 7190 Search PubMed.
  23. F. Aymard, J. Y. Nedelec and J. Périchon, Tetrahedron Lett., 1994, 35, 8623 Search PubMed.
  24. (a) A. R. Amunsden and E. N. Balko, J. Appl. Electrochem., 1992, 22, 810 Search PubMed; (b) S. Torii, P. Liu, N. Bhuvaneswari, C. Amatore and A. Jutand, J. Org. Chem., 1996, 61, 3055 Search PubMed.
  25. J. P. Coleman, R. C. Hallcher, D. E. McMackins, T. E. Rogers and J. H. Wagenknecht, Tetrahedron, 1991, 47, 809 Search PubMed.
  26. E. Oguntoye (née Eru), S. Szunerits, J. H. P. Utley and P. B. Wyatt, Tetrahedron, 1996, 52, 7771 Search PubMed; E. Eru, G. E. Hawkes, J. H. P. Utley and P. B. Wyatt, Tetrahedron, 1995, 51, 3033 Search PubMed.
  27. M. Ihara, A. Katsumata, F. Setsu, Y. Tokunaga and K. Fukumoto, J. Org. Chem., 1996, 61, 677 Search PubMed.
  28. M. Durandetti, J. Y. Nedelec and J. Perichon, J. Org. Chem., 1996, 61, 1748 Search PubMed; S. Condon-Gueugnot, E. Leonel, J. Y. Nedelec and J. Perichon, J. Org. Chem., 1995, 60, 7684 Search PubMed.
  29. C. Amatore, F. Gaubert, A. Jutand and J. H. P. Utley, J. Chem. Soc., Perkin Trans. 2, 1996, 2447 Search PubMed , and refs therein.
  30. C. Combellas, Y. Lu and A. J. Thiebault, Appl. Electrochem., 1993, 23, 841 Search PubMed , and earlier refs..
  31. E. Steckhan, Top. Curr. Chem., 1994, 170, 84 Search PubMed.
  32. C. Demaille, P. R. Unwin and A. J. Bard, J. Phys. Chem., 1996, 100, 14137 Search PubMed , and earlier refs..
  33. F. Zhou and A. J. Bard, J. Am. Chem. Soc., 1994, 116, 393 Search PubMed.
  34. A. J. Fry, R. D. Little and J. Leonetti, J. Org. Chem., 1994, 59, 5017 Search PubMed.
  35. H. Lund, K. Daasbjerg, D. Ochiallini and S. U. Pedersen, Eleektrokhimiya, 1995, 31, 939 Search PubMed.
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