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Photocatalytic Transformations of Organic Substrates Using Inorganic Salts and Complexes

  • U. Kölle
Chapter
Part of the Catalysis by Metal Complexes book series (CMCO, volume 14)

Abstract

In the following reactions are discussed which use UV or visible light and a metal salt or a transition metal complex, in general in less than stoichiometric quantity, to effect an organic substrate transformation. The cases presented are a selection which is intended to illustrate the possibilities — also pitfalls — of this type of photocatalysis. An overview in tabular form can be found in ref. [1]. Not considered is organic photochemistry sensitized by Hg [2] and reactions coupled to excitation of semiconductors. No consideration is given to phototransformations which effect only a change in the metal complex [3] and of the many catalytic reaction cycles which are initiated by ligand loss from a transition metal carbonyl, olefin, alkyl or hydride complex [4]. Informative and timely reviews are available on this topic.

Keywords

Organic Substrate Allyl Alcohol Transition Metal Salt Cycloaddition Product Isomerization Catalyst 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    F. Chanon and M. Chanon: Photocatalysis, Fundamentals and Applications (N. Serpone and E. Pelizzetti eds.), p. 489 ff., John Wiley, New York, 1989.Google Scholar
  2. 2.
    R.H.Crabtree, S.H. Brown, C.A. Mendas, P. Krajnik and R.R. Ferguson: J. Mol. Cat. 74, 85 (1992).CrossRefGoogle Scholar
  3. 3.
    P.C. Ford, D. Wink and D. Dibenedetto: Progr. Inorg. Chem. 30, 213 (1983); A. Vogler and H. Kunkeley: Top.Curr. Chem. 158, 1 (1990); F. Scandola, M.T. Indelli,C. Chiorboli and C.A. Bignozzi: Top. Curr. Chem. 158, 73 (1990); see also J. Chem. Ed. 60, 784 (1983).CrossRefGoogle Scholar
  4. 4.
    G.L. Geoffroy and M.S. Wrighton: Organometallic Photochemistry, Academic Press, New York, 1979; C.G. Kreiter: Adv. Organomet. Chem. 26, 29 (1986); M.D. Rausch, W. Boon and H. Alt: J. Organomet. Chem: 141, 299 (1977).CrossRefGoogle Scholar
  5. 5.
    R.G. Salomon and J.K. Kochi: J. Am. Chem. Soc. 96, 1137 (1974).Google Scholar
  6. 6.
    R.G. Salomon and J.K. Kochi: J. Am. Chem. Soc. 95, 1889 (1973).CrossRefGoogle Scholar
  7. 7.
    P.H.M. Budzelaar, P.J.J.A. Timmermans, A. Mackor and E.J. Baerends: J. Organomet. Chem. 331, 397 (1987).CrossRefGoogle Scholar
  8. 8.
    R. Srinivasan: J. Am. Chem. Soc. 86, 3318 (1964).CrossRefGoogle Scholar
  9. 9.
    R.G. Salomon and N. El Sanadi: J. Am. Chem. Soc. 97, 6214 (1975).CrossRefGoogle Scholar
  10. 10.
    R.S.H. Liu: J. Am. Chem. Soc. 89, 112 (1967).CrossRefGoogle Scholar
  11. 11.
    J.E. Baldwin and R.H. Greeley: J. Am. Chem. Soc. 87, 4514 (1965).CrossRefGoogle Scholar
  12. 12.
    G.M. Whitesides, G.L. Goe and A.C. Cope: J. Am. Chem. Soc. 91, 2608 (1969).CrossRefGoogle Scholar
  13. 13.
    Y.L. Chow, Y. Shen and G. E. Buono-Core: Organometallics 3, 702 (1984).CrossRefGoogle Scholar
  14. 14.
    Y.L. Chow, Xian-en Cheng and G. E. Buono-Core: Organometallics 6, 1126 (1987).CrossRefGoogle Scholar
  15. 15.
    D.J. Trecker, J.P. Henry and J.E. McKeon: J. Am. Chem. Soc. 87, 3261 (1965).CrossRefGoogle Scholar
  16. 16.
    D.J. Trecker, R.S. Foote, J.P. Henry and J.E. McKeon: J. Am. Chem. Soc. 88, 3021 (1966).CrossRefGoogle Scholar
  17. 17.
    A.R. Fraser, P.H. Bird, S.A. Bezman, J.R. Shapley, R. White and J.A. Osbom: J. Am. Chem. Soc. 95, 597 (1973).CrossRefGoogle Scholar
  18. 18.
    R.G. Salomon, K. Folting, W.E. Streib and J.K. Kochi: J. Am. Chem. Soc. 96, 1145 (1974).CrossRefGoogle Scholar
  19. 19.
    J.Th.M. Evers and A. Mackor: Tetrahedron Lett. 21, 415 (1980).CrossRefGoogle Scholar
  20. 20.
    J.Th.M. Evers and A. Mackor: Rec. Tray. Chim. Pays-Bas 98, 423 (1979).CrossRefGoogle Scholar
  21. 21.
    D.P. Schwendiman and C. Kutal: J. Am. Chem. Soc. 99, 5677 (1977); R.F. Sterling and C. Kutal: Inorg. Chem. 19, 1502 (1977).Google Scholar
  22. 22.
    N. Borsub and C. Kutal: J. Am. Chem. Soc. 106, 4826 (1984); K. Yasufuku, K. Takahashi and C. Kutal: Tetrahedron Lett. 25, 4893 (1984).CrossRefGoogle Scholar
  23. 23.
    K. Avasthi, S.R. Raychaudhuri and R.G. Salomon: J. Org . Chem. 49, 4322 (1984).CrossRefGoogle Scholar
  24. 24.
    M. Ohashi, A. Yoshino, K. Yamazaki and T. Yonezawa: Tetrahedron Lett., 3395 (1973).Google Scholar
  25. 25.
    S. Ghosh, S.R. Raychaudhuri and R.G. Salomon: J. Org . Chem. 52, 83 (1987).CrossRefGoogle Scholar
  26. 26.
    J.Th.M. Evers and A. Mackor: Tetrahedron Leu., 821 (1978).Google Scholar
  27. 27.
    R.G. Salomon and A. Sinha: Tetrahedron Lett., 1367 (1978).Google Scholar
  28. T. Sato, K. Tamura, K. Maruyama and O. Ogawa: Tetrahedron Lett.,4221 (1973); T. Sato, K. Tamura, K. Maruyama, O. Ogawa and I. Imamura: J. Chem. Soc. Perkin Trans. 1,779 (1976).Google Scholar
  29. 29.
    T. Sato, K. Yamamoto, K. Fukui, K. Saito, K. Hayakawa and S. Yoshiie: J. Chem. Soc. Perkin Trans. I, 738 (1976).Google Scholar
  30. 30.
    K. Mizuno, J. Ogawa, H. Kagano and Y. Otsuji: Chem. Lett., 437 (1981).Google Scholar
  31. 31.
    M. Asai, H. Matsui and S. Tazuke: Bull. Soc. Chem. Jpn. 47, 864 (1974).CrossRefGoogle Scholar
  32. 32.
    J.W. Breitenbach, F. Sommer and G. Unger: Monatsh.Chem, 101, 32 (1970).CrossRefGoogle Scholar
  33. 33.
    M. Kojima, H. Sakuragi and K. Tokumaru: Bull. Soc. Chem. Jpn. 58, 521 (1985).CrossRefGoogle Scholar
  34. 34.
    G.H. Jones, D.W. Edwards and D. Parr: J. Chem. Soc. Chem. Commun., 969 (1976).Google Scholar
  35. 35.
    R.E. Cameron and A.B. Bocarsly: J. Am. Chem. Soc. 107, 6116 (1985).CrossRefGoogle Scholar
  36. 36.
    W. Strohmeier: Z. Naturforsch. B 29, 282 (1974).Google Scholar
  37. 37.
    S. Lunak, P. Lederer, D. Stopka and J. Veprek-Siska: Collect. Czech. Chem. Commun. 46, 2455 (1981).CrossRefGoogle Scholar
  38. 38.
    A. Sugimori and T. Yamada: Bull. Chem. Soc. Jpn. 59, 3911 (1986).CrossRefGoogle Scholar
  39. 39.
    J. Kagan, P.Y. Juang, B.E. Firth, J.T. Przybytek and S.P. Singh: Tetrahedron Lett., 4289 (1977).Google Scholar
  40. 40.
    K. Araki and S. Shiraishi: Bull. Soc. Chem. Jpn. 59, 229 (1986).CrossRefGoogle Scholar
  41. 41.
    A. Kohda, K. Nagagoshi, K. Maemoto and T. Sato: J. Org . Chem. 48, 425 (1983); T. Sato, T. Oikawa and K. Kobayashi: J. Org . Chem. 50, 1646 (1985).CrossRefGoogle Scholar
  42. 42.
    C.K. Jorgensen and R. Reisfeld: Phys. Chem. Lett. 35, 441 (1975).CrossRefGoogle Scholar
  43. 43.
    N.W. Alcock, N. Herron and T.J. Kemp: J. Chem. Soc. Chem. Commun., 785 (1975).Google Scholar
  44. 44.
    E. Murayama and T. Sato: Bull. Chem. Soc. Jpn. 51, 3022 (1978); E. Murayama, A. Kohda and T. Sato: J. Chem. Soc. Perkin Trans. I, 947 (1980).Google Scholar
  45. 45.
    S.L. Suib, A. Kostapas and D. Psaras: J. Am. Chem. Soc. 106, 1614 (1984).CrossRefGoogle Scholar
  46. 46.
    S.F. Rice and H.B. Gray: J. Am. Chem. Soc. 105, 4571 (1983).CrossRefGoogle Scholar
  47. 47.
    D.M. Roundhill: J. Am. Chem. Soc. 107, 4354 (1985).CrossRefGoogle Scholar
  48. 48.
    C.-M. Che and W.-M. Lee: J. Chem. Soc. Chem. Commun., 512 (1986).Google Scholar
  49. 49.
    N. Zeug, J. Bücheler and H. Kisch: J. Am. Chem. Soc. 107, 1459 (1985); J. Bücheler, N. Zeug and H. Kisch: Angew. Chem. 94, 792 (1982).Google Scholar
  50. 50.
    M.E. Woodhouse, F.D. Lewis and T.J. Marks: J. Am. Chem. Soc. 104, 5586 (1982).CrossRefGoogle Scholar
  51. 51.
    K. Tennakone, U.S. Ketipearachchi, O.A. Ileperuma and S. Punchihewa: J. Mol. Cat. 64, 155 (1991); K. Tennakone, U.S. Ketipearachchi, S. Punchihewa, W.A.C. Perera and R. Tantrigoda: J. Mol. Cat. 65, L1 (1991).CrossRefGoogle Scholar
  52. 52.
    K. Namura, Y. Saito and S. Shinoda: J. Mol. Cat. 50, 303 (1989).CrossRefGoogle Scholar
  53. 53.
    S. Shinoda, H. Moriyama, Y. Kise and Y. Saito: J. Chem. Soc. Chem. Commun., 348 (1978).Google Scholar
  54. 54.
    H.B. Chamann: J. Chem. Soc. B, 584 (1970).Google Scholar
  55. 55.
    G.G. Griggs and D.J.H. Smith: J. Organomet. Chem. 273, 105 (1984).CrossRefGoogle Scholar
  56. 56.
    E. Delgado-Lieta, M.A. Luke, R.F. Jones and D. J. Cole-Hamilton: Polyhedron 1, 839 (1982).CrossRefGoogle Scholar
  57. 57.
    D.A. Wink and P.C. Ford: J. Am.Chem. Soc. 109, 436 (1987).CrossRefGoogle Scholar
  58. 58.
    W. Strohmeier and G. Csontos: J. Organomet. Chem. 72, 277 (1974).CrossRefGoogle Scholar
  59. 59.
    W. Strohmeier and L. Weigelt: J. Organomet. Chem. 82, 417 (1974).CrossRefGoogle Scholar
  60. 60.
    W. Strohmeier and J.-P. Stasch: Z. Naturforsch. B 34, 755 (1979); W. Strohmeier, H. Steigerwald and L. Weigelt: J. Organomet. Chem. 129, 243 (1977).CrossRefGoogle Scholar
  61. 61.
    see for example J.P. Collman and L.S. Hegedus: Principles and Applications of Transition Metal Chemistry, p. 333 ff. and literature cited therein; University Science Books, Mill Valley, 1980.Google Scholar
  62. 62.
    W. Strohmeier and E. Hitzel: J. Organomet. Chem. 87, 353 (1975).CrossRefGoogle Scholar
  63. 63.
    J.R. Peterson, D.W. Bennett and L.D. Spicer: J. Catal. 71, 223 (1981).CrossRefGoogle Scholar
  64. 64.
    E. Samuel: J. Organomet. Chem. 198, C65 (1980).CrossRefGoogle Scholar
  65. 65.
    H. Moriyama, A. Yabe and F. Matsui: J. Mol. Cat. 50, 195 (1989).CrossRefGoogle Scholar
  66. 66.
    B.J. Fisher and R. Eisenberg: Organometallics 2, 764 (1983); A.J. Kunin and R. Eisenberg, J. Am. Chem. Soc. 108, 535 (1986).Google Scholar
  67. 67.
    S. Oishi: J. Mol. Cat. 39, 225 (1987).CrossRefGoogle Scholar
  68. 68.
    U. Koelle: New J. Chem. 16, 157 (1992).Google Scholar
  69. 69.
    G. Pilloni, G. Schiavon, G. Zotti and S. Zecchin: J. Organomet. Chem. 134, 305 (1977).CrossRefGoogle Scholar
  70. 70.
    G. Zotti, S. Zecchin and G. Pilloni: J. Organomet. Chem. 246, 61 (1983).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1993

Authors and Affiliations

  • U. Kölle
    • 1
  1. 1.Institute of Inorganic ChemistryRWTH, Technical University at AachenAachenGermany

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