Advertisement

Reduction of Carbonyl and Other Functional Groups

  • Francis A. Carey
  • Richard J. Sundberg
Part of the Advanced Organic Chemistry book series

Abstract

The most widely used method of adding the elements of hydrogen to a double bond is catalytic hydrogenation. Except for very sterically hindered alkenes, this reaction usually proceeds rapidly and cleanly. The common catalysts are various forms of transition metals, particularly platinum, palladium, rhodium, ruthenium, and nickel. Both the metals, as finely dispersed solids or adsorbed on inert supports such as carbon or alumina, and certain soluble complexes of these metals exhibit catalytic activity. Although carbon—carbon double bonds are the most frequently reduced functional group, many other functionalities are also subject to catalytic hydrogenation under appropriate conditions.

Keywords

Catalytic Hydrogenation Aluminum Hydride Hydride Transfer Lithium Aluminum Hydride Sodium Cyanoborohydride 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

General References

  1. R. L. Augustine (ed.), Reduction Techniques and Applications in Organic Synthesis, Marcel Dekker, New York (1968).Google Scholar
  2. P. N. Rylander, Catalytic Hydrogenation in Organic Syntheses, Academic Press, New York (1979).Google Scholar
  3. M. Freifelder, Catalytic Hydrogenation in Organic Synthesis. Procedures and Commentary, John Wiley and Sons, New York (1978).Google Scholar
  4. B. R. James, Homogeneous Hydrogenation, John Wiley and Sons, New York (1973).Google Scholar
  5. A. Hajos, Complex Hydrides and Related Reducing Agents in Organic Synthesis, Elsevier Scientific, New York (1979).Google Scholar
  6. H. C. Brown, Boranes in Organic Chemistry, Cornell University Press, Ithaca, New York (1972).Google Scholar
  7. A. A. Akhrem, I. G. Rshetova and Y. A. Titov, Birch Reduction of Aromatic Compounds, IFI/Plenum, New York (1972).CrossRefGoogle Scholar
  8. 1a.
    W. R. Roush, J. Am. Chem. Soc. 102, 1390 (1980).CrossRefGoogle Scholar
  9. b. H. C. Brown, S. C. Kim, and S. Krishnamurthy, Error! Hyperlink reference not valid Chem. 45, 1 (1980).Google Scholar
  10. c. G. W. Kabalka, D. T. C. Yang, and J. D. Baker, Jr., Error! Hyperlink reference not valid Chem. 41, 574 (1976).Google Scholar
  11. d. J. K. Whitesell, R. S. Matthews, M. A. Minton, and A. M. Helbling, J. Am. Chem. Soc. 103, 3468 (1981).CrossRefGoogle Scholar
  12. e. K. S. Kim, M. W. Spatz, and F. Johnson, Tetrahedron Lett. 331 (1979).Google Scholar
  13. f. M.-H. Rei, Error! Hyperlink reference not valid Chem. 44, 2760 (1979).Google Scholar
  14. g. R. O. Hutchins, D. Kandasamy, F. Dux, III, C. A. Maryanoff, D. Rotstein, B. Goldsmith, W. Burgoyne, F. Cistone, J. Dalessandro, and J. Puglis, Error! Hyperlink reference not valid Chem. 43, 2259 (1979).Google Scholar
  15. h. H. Lindlar, Hely. Chim. Acta 35, 446 (1952).CrossRefGoogle Scholar
  16. 2.
    D. C. Wigfield and D. J. Phelps, J. Am. Chem. Soc. 96, 543 (1974).CrossRefGoogle Scholar
  17. 3a.
    E. J. Corey, T. K. Schaaf, W. Huber, U. Koelliker, and N. M. Weinshenker, J. Am. Chem. Soc. 92, 397 (1970).CrossRefGoogle Scholar
  18. b. E. J. Corey and R. Noyori, Tetrahedron Lett. 311 (1970).Google Scholar
  19. c. R. F. Borch, Org. Synth. 52, 124 (1972).Google Scholar
  20. d. D. Seyferth and V. A. Mai, J. Am. Chem. Soc. 92, 7412 (1970).CrossRefGoogle Scholar
  21. e. R. V. Stevens and J. T. Lai, Error! Hyperlink reference not valid Chem. 37, 2138 (1972).Google Scholar
  22. f. M. J. Robins and J. S. Wilson, J. Am. Chem. Soc. 103, 932 (1981).CrossRefGoogle Scholar
  23. g. G. R. Pettit and J. R. Dias, Error! Hyperlink reference not valid Chem. 36, 3207 (1971).Google Scholar
  24. h. P. A. Grieco, T. Oguri, and S. Gilman, J. Am. Chem. Soc. 102, 5886 (1980).CrossRefGoogle Scholar
  25. i. M. F. Semmelhack, S. Tomoda, and K. M. Hurst, J. Am. Chem. Soc. 102, 7567 (1980).CrossRefGoogle Scholar
  26. j. H. C. Brown and P. Heim, Error! Hyperlink reference not valid Chem. 38, 912 (1973).Google Scholar
  27. k. R. O. Hutchins and N. R. Natale, Error! Hyperlink reference not valid Chem. 43, 2299 (1978).Google Scholar
  28. l. M. R. Detty and L. A. Paquette, J. Am. Chem. Soc. 99, 821 (1977).CrossRefGoogle Scholar
  29. m. C. A. Bunnell and P. L. Fuchs, J. Am. Chem. Soc. 99, 5184 (1977).CrossRefGoogle Scholar
  30. 4a.
    F. A. Carey, D. H. Ball, and L. Long, Jr., Carbohydr. Res. 3, 205 (1966).CrossRefGoogle Scholar
  31. b. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc. 74, 5828 (1952).CrossRefGoogle Scholar
  32. c. R. N. Rej, C. Taylor, and G. Eadon, Error! Hyperlink reference not valid Chem. 45, 126 (1980).Google Scholar
  33. d. M. C. Dart and H. B. Henbest, J. Chem. Soc. 3563 (1960).Google Scholar
  34. e. E. Piers, W. deWaal, and R. W. Britton, J. Am. Chem. Soc. 93, 5113 (1971).CrossRefGoogle Scholar
  35. f. A. L. J. Beckwith and C. Easton, J. Am. Chem. Soc. 100, 2913 (1978).CrossRefGoogle Scholar
  36. g. D. Horton and W. Weckerle, Carbohydr. Res. 44, 227 (1975).CrossRefGoogle Scholar
  37. 5a.
    D. Lenoir, Synthesis, 553 (1977).Google Scholar
  38. b. J. A. Marshall and A. E. Greene, Error! Hyperlink reference not valid Chem. 36, 2035 (1971).Google Scholar
  39. c. B. M. Trost, Y. Nishimura, and K. Yamamoto, J. Am. Chem. Soc. 101, 1328 (1979)CrossRefGoogle Scholar
  40. J. E. McMurry, A. Andrus, G. M. Ksander, J. H. Musser, and M. A. Johnson, J. Am. Chem. Soc. 101, 1330 (1979).CrossRefGoogle Scholar
  41. d. R. E. Ireland and C. S. Wilcox, Error! Hyperlink reference not valid Chem. 45, 197 (1980).Google Scholar
  42. e. P. G. Gassman and T. J. Atkins, J. Am. Chem. Soc. 94, 7748 (1972).CrossRefGoogle Scholar
  43. f. A. Gopalan and P. Magnus, J. Am. Chem. Soc. 102, 1756 (1980).CrossRefGoogle Scholar
  44. g. R. M. Coates, S. K. Shah, and R. W. Mason, J. Am. Chem. Soc. 101, 6765 (1979)CrossRefGoogle Scholar
  45. Y.-K. Han and L. A. Paquette, Error! Hyperlink reference not valid Chem. 44, 3731 (1979).Google Scholar
  46. h. L. P. Kuhn, J. Am. Chem. Soc. 80, 5950 (1958).CrossRefGoogle Scholar
  47. i. R. P. Hatch, J. Shringarpure, and S. M. Weinreb, Error! Hyperlink reference not valid Chem. 43, 4172 (1978).Google Scholar
  48. j. T. Shono, Y. Matsumura, S. Kashimura, and H. Kyutoku, Tetrahedron Leo. 1205 (1978).Google Scholar
  49. ab. K. E. Wiegers and S. G. Smith, Error! Hyperlink reference not valid Chem. 43, 1126 (1978).Google Scholar
  50. c. D. C. Wigfield and F. W. Gowland, Error! Hyperlink reference not valid Chem. 45, 653 (1980).Google Scholar
  51. 7.
    D. Caine and T. L. Smith, Jr., Error! Hyperlink reference not valid Chem. 43, 755 (1978).Google Scholar
  52. 8.
    R. E. A. Dear and F. L. M. Pattison, J. Am. Chem. Soc. 85, 622 (1963).CrossRefGoogle Scholar
  53. 9a.
    S. Danishefsky, M. Hirama, K. Gombatz, T. Harayama, E. Berman, and P. F. Schuda, J. Am.Chem. Soc. 101, 7020 (1979).CrossRefGoogle Scholar
  54. b. A. S. Kende, M. L. King, and D. P. Curran, Error! Hyperlink reference not valid Chem. 46, 2826 (1981).Google Scholar
  55. c. A. P. Kozikowski and A. Ames, J. Am. Chem. Soc. 103, 3923 (1981).CrossRefGoogle Scholar
  56. 10a.
    H. C. Brown and W. C. Dickason, J. Am. Chem. Soc. 92, 709 (1970).CrossRefGoogle Scholar
  57. b. D. Seyferth, H. Yamazaki, and D. L. Alleston, Error! Hyperlink reference not valid Chem. 28, 703 (1963).Google Scholar
  58. c. G. Stork and S. D. Darling, J. Am. Chem. Soc. 82, 1512 (1960).CrossRefGoogle Scholar
  59. 11a.
    R. F. Borch, Org. Synth. 52, 124 (1972).Google Scholar
  60. b. R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc. 93, 2897 (1971).CrossRefGoogle Scholar
  61. c. A. D. Harmon and C. R. Hutchinson, Tetrahedron Leu. 1293 (1973).Google Scholar
  62. 12.
    S.-K. Chung and F.-F. Chung, Tetrahedron Leu. 2473 (1979).Google Scholar
  63. 13.
    D. F. Taber, Error! Hyperlink reference not valid Chem. 41, 2649 (1976).Google Scholar
  64. 14.
    D. R. Briggs and W. B. Whalley, J. Chem. Soc. Perkin Trans. 1, 1382 (1976).CrossRefGoogle Scholar
  65. 15.
    C. M. Tice and C. H. Heathcock, Error! Hyperlink reference not valid Chem. 46, 9 (1981).Google Scholar
  66. 16a.
    N. J. Leonard and S. Gelfand, J. Am. Chem. Soc. 77, 3272 (1955).CrossRefGoogle Scholar
  67. b. P. S. Wharton and D. H. Bohlen, Error! Hyperlink reference not valid Chem. 26, 3615 (1961)Google Scholar
  68. W. R. Benn and R. M. Dodson, Error! Hyperlink reference not valid Chem. 29, 1142 (1964).Google Scholar
  69. c. G. Lardelli and O. Jeger, Hely. Chim. Acta 32, 1817 (1949).CrossRefGoogle Scholar
  70. d. R. J. Petersen and P. S. Skell, Org. Synth. V, 929 (1973).Google Scholar
  71. 17a.
    N. M. Yoon, C. S. Pak, H. C. Brown, S. Krishnamurthy, and T. P. Stocky, Error! Hyperlink reference not valid Chem. 38, 2786 (1973).Google Scholar
  72. b. D. J. Dawson and R. E. Ireland, Tetrahedron Lett. 1899 (1968).Google Scholar
  73. c. R. O. Hutchins, C. A. Milewski, and B. A. Maryanoff, J. Am. Chem. Soc. 95, 3662 (1973).CrossRefGoogle Scholar
  74. d. M. J. Kornet, P. A. Thio, and S. I. Tan, Error! Hyperlink reference not valid Chem. 33, 3637 (1968).Google Scholar
  75. e. C. T. West, S. J. Donnelly, D. A. Kooistra, and M. P. Doyle, Error! Hyperlink reference not valid Chem. 38, 2675 (1973).Google Scholar
  76. f. M. R. Johnson and B. Rickborn, Error! Hyperlink reference not valid Chem. 35, 1041 (1970).Google Scholar

Copyright information

© Springer Science+Business Media New York 1983

Authors and Affiliations

  • Francis A. Carey
    • 1
  • Richard J. Sundberg
    • 1
  1. 1.University of VirginiaCharlottesvilleUSA

Personalised recommendations