Abstract
A convenient synthesis of functionalized trimethylsilyl aminomethylphosphinates containing triethoxysilyl moieties was developed. Radical addition of bis(trimethylsiloxy)-phosphine to triethoxy(vinyl)silane proceeds regioselectively to afford a novel synthon, (2-triethoxysilylethyl)phosphonite, subsequent aminomethylation of which gives the target phosphinates.
References
V. P. Kukhar, H. R. Hudson, Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity, Wiley, New York, USA, 2000, 634.
S. C. Fields, Tetrahedron, 1999, 55, 12237.
O. I. Kolodiazhnyi, Russ. Chem. Rev., 2006, 75, 227; DOI: https://doi.org/10.1070/RC2006v075n03ABEH001193.
B. Stowasser, K.-H. Budt, L. Jian-Qi, A. Peyman, D. Ruppert, Tetrahedron Lett., 1992, 33, 6625.
M. I. Kabachnik, Yu. B. Shalnev, V. K. Promonenkov, L. V. Kovalenko, T. A. Mastryukova, I. L. Odinets, Methods for the Preparation and Biological Activity of Phosphinothricin and Its Derivatives. Results of Science and Technology. Organic Chemistry, VINITI AS USSR, Moscow, 1988, 8, 110 (in Russian).
M. G. Voronkov, V. M. Dyakov, Silatranes, Nauka, Novosibirsk, 1978, 208 (in Russian).
C. A. Black, J. W. Ucci, J. S. Vorpagel, M. C. Mauck, E. E. Fenlon, Bioorganic Medicinal Chem. Lett., 2002, 12, 3521; DOI: S0960-894X(02)00820-X.
A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, Russ. J. Gen. Chem., 2005, 75, 313; DOI: 1070-3632/05/7502-0313.
V. D. Romanenko, M. V. Shevchuk, V. P. Kukhar, Curr. Org. Chem., 2011, 15, 2774; DOI: 1385-2728/11.
Ya. A. Levin, E. I. Vorkunova, Homolytic Chemistry of Phosphorus, Nauka, Moscow, 1978, 318 (in Russian).
A. I. Rakhimov, Synthesis of Organophosphorus Compounds. Homolytic Reactions, Nauka, Moscow, 1985, 22 (in Russian).
Yu. S. Panova, A. V. Sheyanova, E. V. Baranov, A. N. Kornev, Russ. Chem. Bull., 2020, 69, 132; DOI: https://doi.org/10.1007/s11172-020-2734-6.
Yu. I. Blokhin, I. A. Lubimov, A. M. Bagautdinov, D. K. Gaikov, Russ. Chem. Bull., 2021, 70, 2041; DOI: https://doi.org/10.1007/s11172-021-3315-z.
A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2008, 19, 500; DOI: https://doi.org/10.1002/hc.20469.
A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2017, 28, e21400; DOI: https://doi.org/10.1002/hc.21400.
A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2018, 29, e21419; DOI: https://doi.org/10.1002/hc.21419.
D. Nonhebel, J. Tedder, J. Walton, Radicals, Cambridge Univer Press, Cambridge, 1979, 200.
A. A. Prishchenko, M. V. Livantsov, L. I. Livantsova, D. G. Polshchikov, E. V. Grigoriev, Russ. J. Gen. Chem., 1999, 69, 336; DOI: 1070-3632/99/6902.
E. E. Nifantiev, Chemistry of Hydrophosphoryl Compounds, Nauka, Moscow, 1983, 264 (in Russian).
A. A. Prishchenko, M. V. Livantsov, O. P. Novikova, L. I. Livantsova, V. S. Petrosyan, Heteroatom Chem., 2008, 19, 470; DOI: https://doi.org/10.1002/hc.20448.
A. A. Prishchenko, M. V. Livantsov, V. S. Petrosyan, Russ. J. Gen. Chem., 1994, 64, 1316.
M. G. Voronkov, V. P. Baryshok, L. P. Petukhov, V. I. Rakhlin, R. G. Mirskov, V. A. Pestunovich, J. Organomet. Chem., 1988, 358, 39; DOI: 0022-328X/88/.
L. Wozniak, J. Chojnowski, Tetrahedron, 1989, 45, 2465.
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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.
No human or animal subjects were used in this research.
The authors declare no competing interests.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 1088–1092, April, 2023.
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Prishchenko, A.A., Livantsov, M.V., Novikova, O.P. et al. Synthesis of functionalized trimethylsilyl aminomethylphosphinates containing triethoxysilyl moieties. Russ Chem Bull 72, 1088–1092 (2023). https://doi.org/10.1007/s11172-023-3875-3
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DOI: https://doi.org/10.1007/s11172-023-3875-3