Abstract
Bis(polyfluoroalkyl) chlorophosphites and polyfluoroalkyl dichlorophosphites react easily with secondary amines (from –40 to –22°C, 1–3 h, CH2Cl2) in the presence or absence of triethylamine to form the corresponding bis(polyfluoroalkyl) diorganylamidophosphites or bis(diorganylamido) polyfluoroalkyl phosphites in the yield of up to 74%. Bis(polyfluoroalkyl) diorganylamidophosphites were also synthesized from diorganylamidodichlorophosphites and polyfluoroalkanols (–25 to –22°C, 2 h, Et3N–CH2Cl2) with a yield of 56–60%.
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REFERENCES
Vries, A.H.M., Meetsma, A., and Feringa, B.L., Angew. Chem. Int. Ed., 1996, vol. 35, no. 20, p. 2374. https://doi.org/10.1002/anie.199623741
Feringa, B.L., Pineschi, M., Arnold, L.A., Imbos, R., and Vries, A.H.M., Angew. Chem. Int. Ed., 1997, vol. 36, no. 23, p. 2620. https://doi.org/10.1002/anie.199726201
Franciò, F., Faraone, F., and Leither, W., J. Am. Chem. Soc., 2002, vol. 124, p. 736. https://doi.org/10.1021/ja012099v
Teichert, J.F. and Feringa, B.L., Angew. Chem. Int. Ed., 2010, vol. 49, no. 14, p. 2486. https://doi.org/10.1002/acsami.200904948
Gavrilov, K.N., Chuchelkin, I.V., Zheglov, S.V., Groshkin, N.N., Novikov, I.M., Rastorguev, E.A., and Davankov, V.A., Russ. Chem. Bull., 2011, vol. 60, no. 10, p. 2063. https://doi.org/10.1007/s11172-011-0314-5
Lefort, L. and Vries, J.G., in: Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis, Kamer, P.C.J. and Leeuwen, P.W.N.M., Eds., New York: Wiley, 2012, p. 133. https://doi.org/10.1002/9781118299715
Gavrilov, K.N., Zheglov, S.V., Gavrilov, V.K., Maksimova, M.G., Tafeenko, V.A., Chernyshev, V.V., Birin, K.P., and Mikhel, I.S., Tetrahedron, 2017, vol. 73, no. 5, p. 461. https://doi.org/10.1016/j.tet.2016.12.023
Dabkowski, W., Tworowska, I., Michalski, J., and Cramer, F., J. Chem. Soc. Chem. Commun., 1995, p. 1435. https://doi.org/10.1039/C39950001435
Uzagare, M.C., Claussnitzer, I., Gerrits, M., and Bannwarth, W., ChemBioChem, 2012, vol. 13, p. 2204. https://doi.org/10.1002/cbic.201200528
Durantie, E., Huwiler, S., Leroux, J.-Ch., and Castagner, B., Org. Lett., 2016, vol. 18, no. 13, p. 3162. https://doi.org/10.1021/acs.orglett.6b01374
Jud, L. and Micura, R., Chem. Eur. J., 2016, vol. 23, no. 14, p. 3406. https://doi.org/10.1002/chem.201605056
Michaelides, I.N., Tago, N., Viverge, B., and Carell, T., Chem. Eur. J., 2017, vol. 23, no. 63, p. 15894. https://doi.org/10.1002/chem.201704216
Pujari, S.S. and Tretyakova, N., Chem. Res. Toxic., 2017, vol. 30, no. 1, p. 434. https://doi.org/10.1021/acs.chemrestox.6b00392
Skorenrski, M., Oleksyszyn, J., and Sienrczyk, M., Tetrahedron Lett., 2013, vol. 56, p. 1566. https://doi.org/10.1016/j.tetlet.2013.01.039
Kolomeitsev, A.A., Chabanenko, K.Yu., Röschenthaler, G.-V., and Yagupolskii, Yu.L., Synthesis, 1994, no. 2, p. 145. https://doi.org/10.1055/s-1994-25422
Görg, M., Lork, E., Kolomeitsev, A.A., and Röschenthaler, G.-V., Phosphorus, Sulfur, Silicon, Relat. Elem., 1997, vol. 127, no. 1, p. 15. https://doi.org/10.1080/10426509708040492
Nifantyev, E.E., Koroteev, M.P., Kaziev, G.Z., Zakharova, I.S., Lyssenko, K.A., Kuleshova, L.N., and Antipin, M.Yu., Tetrahedron Lett., 2003, vol. 44, p. 6327. https://doi.org/10.1016/S0040-4039(03)01485-0
Mironov, V.F., Konovalova, I.V., Burnaeva, L.M., and Ofitserov, E.N., Russ. Chem. Rev., 1996, vol. 65, no. 11, p. 935. https://doi.org/10.1070/RC1996v065n11ABEH000270
Pradere, U., Garnier-Amblard, E.C., Coats, S.J., Amblard, F., and Schinazi, R.F., Chem. Rev., 2014, vol. 114, no. 18, p. 9154. https://doi.org/10.1021/cr5002035
Politanskaya, L.V., Selivanova, G.A., Panteleeva, E.V., Tretyakov, E.V., Platonov, V.E., Nikul’shin, P.V., Vinogradov, A.S., Zonov, Ya.V., Karpov, V.M., Mezhenkova, T.V., Vasilyev, A.V., Koldobskii, A.B., Shilova, O.S., Morozova, S.M., Burgart, Ya.V., Shchegolkov, E.V., Saloutin, V.I., Sokolov, V.B., Aksinenko, A.Yu., Nenaidenko, V.G., Moskalik, M.Yu., Astakhova, V.V., Shainyan, B.A., Tabolin, A.A., Ioffe, S.L., Muzalevskiy, V.M., Balenkova, E.S., Shastin, A.V., Tyutyunov, A.A., Boiko, V.E., Igumnov, S.M., Dilman, A.D., Adonin, N.Yu., Bardin, V.V., Masoud, S.M., Vorobyeva, D.V., Osipov, S.N., Nosova, E.V., Lipunova, G.N., Charushin, V.N., Prima, D.O., Makarov, A.G., Zibarev, A.V., Trofimov, B.A., Sobenina, L.N., Belyaeva, K.V., Sosnovskikh, V.Ya., Obydennov, D.L., and Usachev, S.A., Russ. Chem. Rev., 2019, vol. 88, no. 5, p. 425. https://doi.org/10.1070/RCR4871
Romanenko, V.D. and Kukhar, V.P., Tetrahedron, 2008, vol. 64, no. 27, p. 6153. https://doi.org/10.1016/j.tet.2008.04.064
Lin, S., Li, Y., Zheng, Y., Luo, L., Sun, Q., Ge, Z., Cheng, T., and Li, R., Eur. J. Med. Chem., 2017, vol. 127, p. 442. https://doi.org/10.1016/j.ejmech.2016.12.055
Chernyshov, D., Shin, W.-C., Egorov, V., Shatunov, P., Tereshchenko, A., Khasanov, M., Yu, J.-Y., Han, S.-I, Kim, S.-H., Kim, D.-H., Jeong, M.-H., Lee, S.-T., Bae, T.-H., Lee, M.-H., Lee, E.-M., Lee, H.-R., Kim, M.-S., Cho, I.-H., Cho, E.-R., and Choi, D.-M., US Patent 2014/0220426A1, 2014; C. A., 2014, vol. 161, p. 309199.
Jeong, M.-H., Kim, S.-J., Woo, M.-H., Park, H.-J., Kim, M.-S., Cha, S.-Y., Lee, M.-J., Egorov, V., and Shin, W.-Ch., US Patent 2014/0308562 A1, 2014; C. A. 2014, vol. 161, p. 615656
Kormachev, V.V. and Fedoseev, M.S., Preparativnaya khimiya fosfora (Phosphorus Preparative Chemistry), Perm: Ural. Otd. Ross. Akad. Nauk, 1992, p. 77.
Mironov, V.F. and Konovalova, I.V., Zh. Obshch. Khim., 1993, vol. 63, no. 10, p. 2228; C. A., 1994, vol. 121, p. 230861.
Fokin, A.V., Kolomiets, A.F., Komarov, V.A., Rapkin, A.I., Krolevets, A.A., and Pasevina, K.I., Bull. Acad. Sci. USSR. Div. Chem., 1979, vol. 28, no. 1, p. 148. https://doi.org/10.1007/BF00925413
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This work was performed using the equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Federation.
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Malysheva, S.F., Gusarova, N.K., Belogorlova, N.A. et al. Synthesis of Amido- and Diamidophosphites with Polyfluoroalkyl Substituents. Russ J Gen Chem 90, 229–234 (2020). https://doi.org/10.1134/S1070363220020103
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DOI: https://doi.org/10.1134/S1070363220020103