Abstract
Palladium chemistry dominates the catalytic liquid phase oxidation of unsaturated hydrocarbons both in the breadth of commercial processes and in the large number of synthetic applications. Recent work has shown the potential for new routes via oxygen activation chemistry. Control of the oxidation state of Pd catalysts can provide new routes to ally lie oxidation products. Routes to industrially important a,β-unsaturated alcohols, esters and acids occur via both Pd(IV) and Pd(0) intermediates. High oxidation state palladium complexes are implicated in selective catalytic aromatic ring oxidations, while Pd(II) intermediates give rise to oxidative coupling, and low oxidation state species are responsible for benzylic oxidations.
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References
P. M. Henry, “Palladium Catalyzed Oxidation of Hydrocarbons”, D. Reidel Publishing Company, Boston, (1980).
P. M. Maitlis, “The Organic Chemistry of Palladium, Vol. II Catalytic Reactions”, Academic Press, New York, (1971).
S. Otsuka, A. Nakamura and Y. Tatsuno, Chem. Commun. 836 (1967).
S. Otsuka, A. Nakamura and Y. Tatsuno, J. Amer. Chem. Soc., 91: 6994 (1969).
J. J. Levison and S. D. Robinson, J. Chem. Soc. A., 762 (1971)
R. A. Sheldon and J. A. Van Doom, J. Organometal. Chem., 94:115 (1975).
F. Igersheim and H. Mimoun, Nov. J. Chim., 4:711 (1980).
M. Roussel and H. Mimoun, J. Org. Chem. 45:5381 (1980).
M. Andrews and K. Kelley, J. Amer. Chem. Soc., 103:2894 (1981).
J. D. Solar, F. Mares, and S. E. Diamond, Catal. Rev. Sci. Eng., 27:1 (1985).
J. E. Lyons, “Applied Industrial Catalyst - Vol. 3” B.E. Leach, Ed., Academic Press, New York, 1984, p. 134.
E. Stern, Catal. Rev., 1:73 (1968).
J. E. Lyons, “Homogeneous and Heterogeneous Catalysis” Yu. Yermakov and V. Likholobov, Eds., VNU Science Press, Utrecht, The Netherlands, (1986) pp 117–138.
A. D. Ketley and J. Braatz, Chem. Commun., 169 (1968).
S. Winstein, J. McCaskie, H.-B. Lee and P. M. Henry, J. Am.Chem. Soc., 98:6913 (1978).
I. P. Stolyarov, M. N. Vargaftik, O. M. Nefedov and I. I. Moiseev, Kinetika i Kataliz, 23:376 (1982).
W. Swodenk and G. Scharfe, U.S. Patent 3,925,452 (1975).
B. M. Trost and P. J. Metzner, J. Am. Chem. Soc., 102:3572 (1980).
L. Saussine, J.-P. Laloz and H. Mimoun, French Patent 2,450,802 (1980).
T. Seiyama, N. Yamazoe, J. Hojo and M. Hayakawa, J. Catal., 739 (1974).
K. Fujimoto and T. Kunugi, J. Jgn. Petrol. Inst., 17:739 (1974).
R. David and J. Estienne, U.S. Patent 3,624,147 (1971).
J. A. Hinnenkamp, U.S. Patent 4,435,598 (1984).
P. M. Henry, J. Org. Chem., 36:1886 (1971).
L. Eberson and L. Gomez-Gonzalez, Act. Chem. Scand., 27:1162 (1973); 27:1249 (1973); 27:1253 (1973).
L. Eberson and L. Jonsson, Act. Chem. Scand., 28:597 (1974); 28:771 (1974); 30:361 (1976).
L. Eberson and L. Jonsson, Act. Chem. Scand., 28:771 (1974); Liebigs Ann. Chem., 233 (1977).
L. M. Stock, K. Tse, L. J. Vorvick and S. A. Walstrum, J. Org. Chem., 46:1759 (1981).
R. Van Helden and G. Verberg, Rec. Trav. Chim., 84:1263 (1965).
M. O. Unger and R. A. Fouty, J. Org. Chem., 34:18 (1969).
F. R. S. Clark, R. O. C. Norman, C. B. Thomas and J. S. Willson, J.C.S. Perkin I, 1289 (1974).
H. Iataaki and H. Yoshimoto, J. Org. Chem., 38:76 (1973).
H. Itatani and H. Yoshimoto, Chem. Ind., 674 (1971).
A. I. Rudenkov, G. U. Mennenga, L. N. Rachkovskaya, K. I. Matveev and I. V. Kozhevnikov, Kinet. i Katal., 18:915 (1977).
Y. Itahara, Chem. Ind., 330 (1982).
V.H.-J. Arpe and L. Hornig, Erdol und Kohle, 23:79 (1970).
I. V. Kozhenikov and K. I. Matveev, Applied Catalysis, 5:135 (1985).
D. R. Bryant, J. E. McKeon and B. C. Ream, Tetrahedron Lett., 3371 (1968); J. Org. Chem., 33:4123 (1968).
M. K. Starchevskii, M. N. Vargaftik and I. I. Moiseev, Kinetika i Kataliz, 20:1163 (1979).
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© 1988 Plenum Press, New York
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Lyons, J.E. (1988). Dependence of Reaction Pathways and Product Distribution on the Oxidation State of Palladium Catalysts for the Reactions of Olefinic and Aromatic Substrates with Molecular Oxygen. In: Martell, A.E., Sawyer, D.T. (eds) Oxygen Complexes and Oxygen Activation by Transition Metals. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0955-0_17
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DOI: https://doi.org/10.1007/978-1-4613-0955-0_17
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