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.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
General References
R. L. Augustine (ed.), Reduction Techniques and Applications in Organic Synthesis, Marcel Dekker, New York (1968).
P. N. Rylander, Catalytic Hydrogenation in Organic Syntheses, Academic Press, New York (1979).
M. Freifelder, Catalytic Hydrogenation in Organic Synthesis. Procedures and Commentary, John Wiley and Sons, New York (1978).
B. R. James, Homogeneous Hydrogenation, John Wiley and Sons, New York (1973).
A. Hajos, Complex Hydrides and Related Reducing Agents in Organic Synthesis, Elsevier Scientific, New York (1979).
H. C. Brown, Boranes in Organic Chemistry, Cornell University Press, Ithaca, New York (1972).
A. A. Akhrem, I. G. Rshetova and Y. A. Titov, Birch Reduction of Aromatic Compounds, IFI/Plenum, New York (1972).
W. R. Roush, J. Am. Chem. Soc. 102, 1390 (1980).
b. H. C. Brown, S. C. Kim, and S. Krishnamurthy, Error! Hyperlink reference not valid Chem. 45, 1 (1980).
c. G. W. Kabalka, D. T. C. Yang, and J. D. Baker, Jr., Error! Hyperlink reference not valid Chem. 41, 574 (1976).
d. J. K. Whitesell, R. S. Matthews, M. A. Minton, and A. M. Helbling, J. Am. Chem. Soc. 103, 3468 (1981).
e. K. S. Kim, M. W. Spatz, and F. Johnson, Tetrahedron Lett. 331 (1979).
f. M.-H. Rei, Error! Hyperlink reference not valid Chem. 44, 2760 (1979).
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).
h. H. Lindlar, Hely. Chim. Acta 35, 446 (1952).
D. C. Wigfield and D. J. Phelps, J. Am. Chem. Soc. 96, 543 (1974).
E. J. Corey, T. K. Schaaf, W. Huber, U. Koelliker, and N. M. Weinshenker, J. Am. Chem. Soc. 92, 397 (1970).
b. E. J. Corey and R. Noyori, Tetrahedron Lett. 311 (1970).
c. R. F. Borch, Org. Synth. 52, 124 (1972).
d. D. Seyferth and V. A. Mai, J. Am. Chem. Soc. 92, 7412 (1970).
e. R. V. Stevens and J. T. Lai, Error! Hyperlink reference not valid Chem. 37, 2138 (1972).
f. M. J. Robins and J. S. Wilson, J. Am. Chem. Soc. 103, 932 (1981).
g. G. R. Pettit and J. R. Dias, Error! Hyperlink reference not valid Chem. 36, 3207 (1971).
h. P. A. Grieco, T. Oguri, and S. Gilman, J. Am. Chem. Soc. 102, 5886 (1980).
i. M. F. Semmelhack, S. Tomoda, and K. M. Hurst, J. Am. Chem. Soc. 102, 7567 (1980).
j. H. C. Brown and P. Heim, Error! Hyperlink reference not valid Chem. 38, 912 (1973).
k. R. O. Hutchins and N. R. Natale, Error! Hyperlink reference not valid Chem. 43, 2299 (1978).
l. M. R. Detty and L. A. Paquette, J. Am. Chem. Soc. 99, 821 (1977).
m. C. A. Bunnell and P. L. Fuchs, J. Am. Chem. Soc. 99, 5184 (1977).
F. A. Carey, D. H. Ball, and L. Long, Jr., Carbohydr. Res. 3, 205 (1966).
b. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc. 74, 5828 (1952).
c. R. N. Rej, C. Taylor, and G. Eadon, Error! Hyperlink reference not valid Chem. 45, 126 (1980).
d. M. C. Dart and H. B. Henbest, J. Chem. Soc. 3563 (1960).
e. E. Piers, W. deWaal, and R. W. Britton, J. Am. Chem. Soc. 93, 5113 (1971).
f. A. L. J. Beckwith and C. Easton, J. Am. Chem. Soc. 100, 2913 (1978).
g. D. Horton and W. Weckerle, Carbohydr. Res. 44, 227 (1975).
D. Lenoir, Synthesis, 553 (1977).
b. J. A. Marshall and A. E. Greene, Error! Hyperlink reference not valid Chem. 36, 2035 (1971).
c. B. M. Trost, Y. Nishimura, and K. Yamamoto, J. Am. Chem. Soc. 101, 1328 (1979)
J. E. McMurry, A. Andrus, G. M. Ksander, J. H. Musser, and M. A. Johnson, J. Am. Chem. Soc. 101, 1330 (1979).
d. R. E. Ireland and C. S. Wilcox, Error! Hyperlink reference not valid Chem. 45, 197 (1980).
e. P. G. Gassman and T. J. Atkins, J. Am. Chem. Soc. 94, 7748 (1972).
f. A. Gopalan and P. Magnus, J. Am. Chem. Soc. 102, 1756 (1980).
g. R. M. Coates, S. K. Shah, and R. W. Mason, J. Am. Chem. Soc. 101, 6765 (1979)
Y.-K. Han and L. A. Paquette, Error! Hyperlink reference not valid Chem. 44, 3731 (1979).
h. L. P. Kuhn, J. Am. Chem. Soc. 80, 5950 (1958).
i. R. P. Hatch, J. Shringarpure, and S. M. Weinreb, Error! Hyperlink reference not valid Chem. 43, 4172 (1978).
j. T. Shono, Y. Matsumura, S. Kashimura, and H. Kyutoku, Tetrahedron Leo. 1205 (1978).
ab. K. E. Wiegers and S. G. Smith, Error! Hyperlink reference not valid Chem. 43, 1126 (1978).
c. D. C. Wigfield and F. W. Gowland, Error! Hyperlink reference not valid Chem. 45, 653 (1980).
D. Caine and T. L. Smith, Jr., Error! Hyperlink reference not valid Chem. 43, 755 (1978).
R. E. A. Dear and F. L. M. Pattison, J. Am. Chem. Soc. 85, 622 (1963).
S. Danishefsky, M. Hirama, K. Gombatz, T. Harayama, E. Berman, and P. F. Schuda, J. Am.Chem. Soc. 101, 7020 (1979).
b. A. S. Kende, M. L. King, and D. P. Curran, Error! Hyperlink reference not valid Chem. 46, 2826 (1981).
c. A. P. Kozikowski and A. Ames, J. Am. Chem. Soc. 103, 3923 (1981).
H. C. Brown and W. C. Dickason, J. Am. Chem. Soc. 92, 709 (1970).
b. D. Seyferth, H. Yamazaki, and D. L. Alleston, Error! Hyperlink reference not valid Chem. 28, 703 (1963).
c. G. Stork and S. D. Darling, J. Am. Chem. Soc. 82, 1512 (1960).
R. F. Borch, Org. Synth. 52, 124 (1972).
b. R. F. Borch, M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc. 93, 2897 (1971).
c. A. D. Harmon and C. R. Hutchinson, Tetrahedron Leu. 1293 (1973).
S.-K. Chung and F.-F. Chung, Tetrahedron Leu. 2473 (1979).
D. F. Taber, Error! Hyperlink reference not valid Chem. 41, 2649 (1976).
D. R. Briggs and W. B. Whalley, J. Chem. Soc. Perkin Trans. 1, 1382 (1976).
C. M. Tice and C. H. Heathcock, Error! Hyperlink reference not valid Chem. 46, 9 (1981).
N. J. Leonard and S. Gelfand, J. Am. Chem. Soc. 77, 3272 (1955).
b. P. S. Wharton and D. H. Bohlen, Error! Hyperlink reference not valid Chem. 26, 3615 (1961)
W. R. Benn and R. M. Dodson, Error! Hyperlink reference not valid Chem. 29, 1142 (1964).
c. G. Lardelli and O. Jeger, Hely. Chim. Acta 32, 1817 (1949).
d. R. J. Petersen and P. S. Skell, Org. Synth. V, 929 (1973).
N. M. Yoon, C. S. Pak, H. C. Brown, S. Krishnamurthy, and T. P. Stocky, Error! Hyperlink reference not valid Chem. 38, 2786 (1973).
b. D. J. Dawson and R. E. Ireland, Tetrahedron Lett. 1899 (1968).
c. R. O. Hutchins, C. A. Milewski, and B. A. Maryanoff, J. Am. Chem. Soc. 95, 3662 (1973).
d. M. J. Kornet, P. A. Thio, and S. I. Tan, Error! Hyperlink reference not valid Chem. 33, 3637 (1968).
e. C. T. West, S. J. Donnelly, D. A. Kooistra, and M. P. Doyle, Error! Hyperlink reference not valid Chem. 38, 2675 (1973).
f. M. R. Johnson and B. Rickborn, Error! Hyperlink reference not valid Chem. 35, 1041 (1970).
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1983 Springer Science+Business Media New York
About this chapter
Cite this chapter
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
Download citation
DOI: https://doi.org/10.1007/978-1-4757-1821-8_5
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4757-1823-2
Online ISBN: 978-1-4757-1821-8
eBook Packages: Springer Book Archive