Abstract
A new approach to phosphorylation of benzene with diethyl phosphite is suggested, which is based on the electrocatalytic oxidation of a mixture of benzene and diethyl phosphite (1 : 1) under mild conditions (room temperature, normal pressure) in the presence of bimetallic catalytic systems MnII/CoIIL (MnSO4/CoCl2dmphen or MnCl2/CoCl2bipy). This method gives diethyl phenylphosphonate in high yield (up to 90%) and practically 100% conversion of the phosphite.
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References
G. M. Kosolapoff, L. Maier, Organic Phosphorus Compounds, Wiley-Interscience, New York, 1972, V. 1—7.
D. E. C. Corbridge, in Phosphorus: Chemistry, Biochemistry and Technology, 6th ed., CRC Press, London, 2013, 1473 pp.
S. Swaminathan, K. V. Narayanan, Chem. Rev., 1971, 71, 429.
A. K. Bhattacharya, G. Thyagarajan, Chem. Rev., 1981, 81, 415.
R. Engel, J. I. Cohen, Synthesis of Carbon—Phosphorus Bonds, 2nd ed., CRC Press, Lomdon, 2004, 187 pp.
P. Tavs, Chem. Ber., 1970, 103, 2428.
J. A. Connor, A. C. Jones, J. Chem. Soc., Chem. Commun., 1980, 137.
N. Hall, R. Proce, J. Chem. Soc., Perkin Trans. 1, 1979, 2634.
T. Hirao, T. Masunaga, Y. Oshiro, T. Agawa, Synthesis, 1981, 56.
T. Hirao, T. Masunaga, N. Yamada, Y. Oshiro, T. Agawa, Bull. Chem. Soc. Jpn, 1982, 55, 909.
S. Battagia, S. Vyle, Tetrahedron Lett., 2003, 44, 861.
R. Obrycki, C. E. Griffin, J. Org. Chem., 1968, 33, 632.
J. F. Bunnet, X. Creary, J. Org. Chem., 1974, 39, 3612.
E. F. Jason, E. K. Fields, J. Org. Chem., 1962, 27, 1402.
H. Kottman, J. Skarzewski, F. Effenberger, Synthesis, 1987, 797.
F. Effenberger, H. Kottmann, Tetrahedron, 1985, 41, 4171.
T. Kagayama, A. Nakano, S. Sakaguchi, Y. Ishii, Org. Lett., 2006, 8, 407.
H. Ohmori, S. Nakai, M. Masui, J. Chem. Soc., Perkin Trans. 1, 1979, 2023.
E. V. Nikitin, A. S. Romakhin, O. V. Parakin, G. V. Romanov, Yu. M. Kargin, A. N. Pudovik, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 566 [Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 626].
H. Cruz, I. Gallardo, G. Guirado, Eur. J. Org. Chem., 2011, 36, 7378.
X. Mao, X. Ma, S. Zhang, H. Hu, C. Zhu, Y. Cheng, Eur. J. Org. Chem., 2013, 20, 4245.
A. Jutand, Chem. Rev., 2008, 108, 2300.
Yu. H. Budnikova, Russ. Chem. Rev., 2002, 71, 111.
N. P. Burkovskaya, M. E. Nikiforova, M. A. Kiskin, A. S. Lermontov, A. S. Bogomyakov, V. S. Mironov, I. L. Eremenko, Polyhedron, 2011, 30, 2941.
X. R. Lan, F. Wu, D. Y. Ji, J. M. Feng, Z. Y. Liu, M. B. Yang, Acta Polymer. Sinica, 2013, 8, 002.
V. V. Kormachev, M. S. Fedoseev, Preparativnaya khimiya fosfora [Preparative Phosphorus Chemistry], UrORAN, Perm´, 1992, 69 (in Russian).
M. J. Hynes, P. F. Brannick, Inorg. Chim. Acta, 1979, 33, 11.
G. Muller, J. Sales, J. Vinaixa, J. Org. Chem., 1984, 273, 255.
Y. G. Budnikova, D. I. Tazeev, A. G. Kafiyatullina, D. G. Yakhvarov, V. I. Morozov, N. K. Gusarova, B. A. Trofimov, O. G. Sinyashin, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 942 [Izv. Akad. Nauk, Ser. Khim., 2005, 919].
M. C. Kohler, J. G. Sokol, Jr., R. A. Stockland, Tetrahedron Lett., 2009, 50, 457.
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Based on the materials of the XXVI International Chugaev Conference on Coordination Chemistry (October 6—10, 2014, Kazan).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1926—1932, August, 2015.
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Khrizanforov, M.N., Strekalova, S.O., Gryaznova, T.V. et al. New method of metal-induced oxidative phosphorylation of benzene. Russ Chem Bull 64, 1926–1932 (2015). https://doi.org/10.1007/s11172-015-1095-z
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DOI: https://doi.org/10.1007/s11172-015-1095-z