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Reduction of Carbonyl and Other Functional Groups

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Part of the book series: Advanced Organic Chemistry

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.

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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).

    Book  Google Scholar 

  8. W. R. Roush, J. Am. Chem. Soc. 102, 1390 (1980).

    Article  Google Scholar 

  9. b. H. C. Brown, S. C. Kim, and S. Krishnamurthy, Error! Hyperlink reference not valid Chem. 45, 1 (1980).

    CAS  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).

    CAS  Google Scholar 

  11. d. J. K. Whitesell, R. S. Matthews, M. A. Minton, and A. M. Helbling, J. Am. Chem. Soc. 103, 3468 (1981).

    Article  CAS  Google 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).

    Article  Google Scholar 

  16. D. C. Wigfield and D. J. Phelps, J. Am. Chem. Soc. 96, 543 (1974).

    Article  CAS  Google Scholar 

  17. E. J. Corey, T. K. Schaaf, W. Huber, U. Koelliker, and N. M. Weinshenker, J. Am. Chem. Soc. 92, 397 (1970).

    Article  CAS  Google 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).

    Article  CAS  Google Scholar 

  21. e. R. V. Stevens and J. T. Lai, Error! Hyperlink reference not valid Chem. 37, 2138 (1972).

    CAS  Google Scholar 

  22. f. M. J. Robins and J. S. Wilson, J. Am. Chem. Soc. 103, 932 (1981).

    Article  CAS  Google Scholar 

  23. g. G. R. Pettit and J. R. Dias, Error! Hyperlink reference not valid Chem. 36, 3207 (1971).

    CAS  Google Scholar 

  24. h. P. A. Grieco, T. Oguri, and S. Gilman, J. Am. Chem. Soc. 102, 5886 (1980).

    Article  CAS  Google Scholar 

  25. i. M. F. Semmelhack, S. Tomoda, and K. M. Hurst, J. Am. Chem. Soc. 102, 7567 (1980).

    Article  CAS  Google Scholar 

  26. j. H. C. Brown and P. Heim, Error! Hyperlink reference not valid Chem. 38, 912 (1973).

    CAS  Google Scholar 

  27. k. R. O. Hutchins and N. R. Natale, Error! Hyperlink reference not valid Chem. 43, 2299 (1978).

    CAS  Google Scholar 

  28. l. M. R. Detty and L. A. Paquette, J. Am. Chem. Soc. 99, 821 (1977).

    Article  CAS  Google Scholar 

  29. m. C. A. Bunnell and P. L. Fuchs, J. Am. Chem. Soc. 99, 5184 (1977).

    Article  CAS  Google Scholar 

  30. F. A. Carey, D. H. Ball, and L. Long, Jr., Carbohydr. Res. 3, 205 (1966).

    Article  CAS  Google Scholar 

  31. b. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc. 74, 5828 (1952).

    Article  CAS  Google Scholar 

  32. c. R. N. Rej, C. Taylor, and G. Eadon, Error! Hyperlink reference not valid Chem. 45, 126 (1980).

    CAS  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).

    Article  CAS  Google Scholar 

  35. f. A. L. J. Beckwith and C. Easton, J. Am. Chem. Soc. 100, 2913 (1978).

    Article  CAS  Google Scholar 

  36. g. D. Horton and W. Weckerle, Carbohydr. Res. 44, 227 (1975).

    Article  CAS  Google Scholar 

  37. 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).

    CAS  Google Scholar 

  39. c. B. M. Trost, Y. Nishimura, and K. Yamamoto, J. Am. Chem. Soc. 101, 1328 (1979)

    Article  CAS  Google Scholar 

  40. J. E. McMurry, A. Andrus, G. M. Ksander, J. H. Musser, and M. A. Johnson, J. Am. Chem. Soc. 101, 1330 (1979).

    Article  CAS  Google Scholar 

  41. d. R. E. Ireland and C. S. Wilcox, Error! Hyperlink reference not valid Chem. 45, 197 (1980).

    CAS  Google Scholar 

  42. e. P. G. Gassman and T. J. Atkins, J. Am. Chem. Soc. 94, 7748 (1972).

    Article  Google Scholar 

  43. f. A. Gopalan and P. Magnus, J. Am. Chem. Soc. 102, 1756 (1980).

    Article  CAS  Google Scholar 

  44. g. R. M. Coates, S. K. Shah, and R. W. Mason, J. Am. Chem. Soc. 101, 6765 (1979)

    Article  CAS  Google Scholar 

  45. Y.-K. Han and L. A. Paquette, Error! Hyperlink reference not valid Chem. 44, 3731 (1979).

    CAS  Google Scholar 

  46. h. L. P. Kuhn, J. Am. Chem. Soc. 80, 5950 (1958).

    Article  Google Scholar 

  47. i. R. P. Hatch, J. Shringarpure, and S. M. Weinreb, Error! Hyperlink reference not valid Chem. 43, 4172 (1978).

    CAS  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).

    CAS  Google Scholar 

  50. c. D. C. Wigfield and F. W. Gowland, Error! Hyperlink reference not valid Chem. 45, 653 (1980).

    CAS  Google Scholar 

  51. D. Caine and T. L. Smith, Jr., Error! Hyperlink reference not valid Chem. 43, 755 (1978).

    CAS  Google Scholar 

  52. R. E. A. Dear and F. L. M. Pattison, J. Am. Chem. Soc. 85, 622 (1963).

    Article  CAS  Google Scholar 

  53. S. Danishefsky, M. Hirama, K. Gombatz, T. Harayama, E. Berman, and P. F. Schuda, J. Am.Chem. Soc. 101, 7020 (1979).

    Article  CAS  Google Scholar 

  54. b. A. S. Kende, M. L. King, and D. P. Curran, Error! Hyperlink reference not valid Chem. 46, 2826 (1981).

    CAS  Google Scholar 

  55. c. A. P. Kozikowski and A. Ames, J. Am. Chem. Soc. 103, 3923 (1981).

    Article  CAS  Google Scholar 

  56. H. C. Brown and W. C. Dickason, J. Am. Chem. Soc. 92, 709 (1970).

    Article  CAS  Google Scholar 

  57. b. D. Seyferth, H. Yamazaki, and D. L. Alleston, Error! Hyperlink reference not valid Chem. 28, 703 (1963).

    CAS  Google Scholar 

  58. c. G. Stork and S. D. Darling, J. Am. Chem. Soc. 82, 1512 (1960).

    Article  CAS  Google Scholar 

  59. 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).

    Article  CAS  Google Scholar 

  61. c. A. D. Harmon and C. R. Hutchinson, Tetrahedron Leu. 1293 (1973).

    Google Scholar 

  62. S.-K. Chung and F.-F. Chung, Tetrahedron Leu. 2473 (1979).

    Google Scholar 

  63. D. F. Taber, Error! Hyperlink reference not valid Chem. 41, 2649 (1976).

    Google Scholar 

  64. D. R. Briggs and W. B. Whalley, J. Chem. Soc. Perkin Trans. 1, 1382 (1976).

    Article  Google Scholar 

  65. C. M. Tice and C. H. Heathcock, Error! Hyperlink reference not valid Chem. 46, 9 (1981).

    CAS  Google Scholar 

  66. N. J. Leonard and S. Gelfand, J. Am. Chem. Soc. 77, 3272 (1955).

    Article  CAS  Google Scholar 

  67. b. P. S. Wharton and D. H. Bohlen, Error! Hyperlink reference not valid Chem. 26, 3615 (1961)

    CAS  Google Scholar 

  68. W. R. Benn and R. M. Dodson, Error! Hyperlink reference not valid Chem. 29, 1142 (1964).

    CAS  Google Scholar 

  69. c. G. Lardelli and O. Jeger, Hely. Chim. Acta 32, 1817 (1949).

    Article  CAS  Google Scholar 

  70. d. R. J. Petersen and P. S. Skell, Org. Synth. V, 929 (1973).

    Google Scholar 

  71. N. M. Yoon, C. S. Pak, H. C. Brown, S. Krishnamurthy, and T. P. Stocky, Error! Hyperlink reference not valid Chem. 38, 2786 (1973).

    CAS  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).

    Article  CAS  Google Scholar 

  74. d. M. J. Kornet, P. A. Thio, and S. I. Tan, Error! Hyperlink reference not valid Chem. 33, 3637 (1968).

    CAS  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).

    CAS  Google Scholar 

  76. f. M. R. Johnson and B. Rickborn, Error! Hyperlink reference not valid Chem. 35, 1041 (1970).

    CAS  Google Scholar 

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Carey, F.A., Sundberg, R.J. (1983). Reduction of Carbonyl and Other Functional Groups. In: Advanced Organic Chemistry. Advanced Organic Chemistry. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-1821-8_5

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  • DOI: https://doi.org/10.1007/978-1-4757-1821-8_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4757-1823-2

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