Abstract
The hydrogenolysis of the C-O bond in monoaryl sulfates by the action of an excess of NaH2PO2 in the presence of catalytic amounts of PdCl2 and KOH is studied. The reaction proceeds chemoselectively with complete ester conversion to the corresponding arenes.
References
J. I. DeGraw, J. C. Christinsen, V. H. Brown, and M. J. Cory,J. Heterocycl. Chem., 1974,11, 363.
S. Sakai, A. Kubo, T. Hamamoto, M. Wakabayashi, K. Takahashi, J. Haginiva, and Y. Ohtani,Tetrahedron Lett., 1969,19, 1489.
C. F. Barfknecht, R. V. Smith, and V. D. Reif,Can. J. Chem., 1970,48, 2138.
H. C. Beyerman, E. Buurman, T. S. Lie, and L. Maat,Rec'. Trav. Chim. Pays-Bas, 1976,95, 43.
L. R. Subramanian, A. G. Martinez, A. H. Fernandez, and R. M. Alvarez,Synthesis, 1984, 143, N574-016, 481.
S. Cacci, P. Gp Giattini, E. Morrera, and G. Ortar,Tetrahedron Lett., 1986,27, 5541.
Q. Y. Chen and Y. B. He,Synthesis, 1988, 896.
B. J. Hassey, R. A. W. Johnstone, and I. D. Entwistle,Tetrahedron, 1982,38, 3775.
G. A. Peterson, F. A. Kunng, J. S. McCallum, and W. D. Wulf,Tetrahedron Lett., 1987,28, 1380.
E. Vowinkel and H. J. Baese,Chem. Ber., 1974,107, 1213.
E. Vowinkel and C. Wolff,Chem. Ber., 1974,107, 907.
J. D. Weaver, E. J. Eisenbraun, and L. E. Harris,Chem. Ind. (London), 1973, 187.
W. J. Musliner and J. W. Gates,J. Am. Chem. Soc., 1966,88, 4271.
T. Shono, Y. Matsumoto, K. Tsubata, and Y. Sugihara,J. Org. Chem., 1979,44, 4508.
W. Lonsky, H. Traitler, and K. Kratzl,J. Chem. Soc., Perkin Trans., 1, 1975, 169.
D. V. Davydov and I. P. Beletskaya,Metalloorg. Khim., 1983,6, 11. [J. Organomet. Chem. USSR, 1983,6 (Erigl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 605–606, March, 1993.
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Davydov, D.V., Beletskaya, I.P. PdCl2-catalyzed hydrogenolysis of a C-O bond in monoaryl sulfates by sodium phosphinate in an aqueous alkaline medium. Russ Chem Bull 42, 573–575 (1993). https://doi.org/10.1007/BF00698458
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DOI: https://doi.org/10.1007/BF00698458