Abstract
The main deuterium and tritium sources used for preparing hydrogen isotope labeled compounds are presented. The mechanisms of hydrogenation and isotope exchange in organic compounds in the presence of heterogeneous and homogeneous catalysts when using gaseous tritium (or deuterium) or tritium (or deuterium) water are considered. Examples of the participation of solvent protons in introduction of deuterium and tritium into organic compounds by dehalogenation are presented. The problem of selective hydrogenation and dehalogenation is briefly discussed. Particular attention is paid to isotope exchange with deuterium or tritium in the presence of homogeneous iridium catalysts.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Isin, E.M., Elmore, C.S., Nilsson, G.N., et al., Chem. Res. Toxicol., 2012, vol. 25, no. 3, pp. 532–542.
Allen, P.H., Hickey, M.J., Kingston, L.P., and Wilkinson, D.J., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 731–738.
Shevchenko, V.P., Nagaev, I.Yu., Pronina, T.S., et al., Dokl. Chem., 2018, vol. 480, no. 2, pp. 117–120.
Lockley, W.J.S., McEwen, A., and Cooke,. R., J. Label. Compd. Radiopharm., 2012, vol. 55, no. 7, pp. 235–257.
Lin, D.-L., Chang, W.-T., Kuo, T. L., and Liu, R.H., J. Anal. Toxicol., 2000, vol. 24, no. 4, pp. 275–280.
Atzrodt, J. and Derdau, V., J. Label. Compd. Radio-pharm., 2010, vol. 53, nos. 11–12, pp. 674–685.
Parkin, G., J. Label. Compd. Radiopharm., 2007, vol. 50, nos. 11–12, pp. 1088–1114.
Heinekey, D.M., J. Label. Compd. Radiopharm., 2007, vol. 50, nos. 11–12, pp. 1063–1071.
Quasdorf, K.W., Huters, A.D., Lodewyk, M.W., et al., J. Am. Chem. Soc., 2012, vol. 134, no. 3, pp. 1396–1399.
Evans, E.A., Tritium and Its Compounds, London: But-terworths, 1974.
Hinz, H.R., Harris, N.J., Giovanella, B.C., et al., J. Label. Compd. Radiopharm., 1996, vol. 38, no. 8, pp. 733–742.
Samonina-Kosicka, J. and Kanska, M., J. Label. Compd. Radiopharm., 2013, vol. 56, no. 6, pp. 317–320.
Jian, Z., Ray, T., Wu, A., and Jones, L., J. Label. Compd. Radiopharm., 2012, vol. 55, no. 2, pp. 84–87.
Kolbe, A., Schneider, B., Voigt, B., and Adam, G., J. Label. Compd. Radiopharm., 1998, vol. 41, no. 2, pp. 131–137.
Kanska, M., J. Radioanal. Nucl. Chem., 1988, vol. 125, no. 1, pp. 183–188.
McGeady, P. and Croteau, R., J. Chem. Soc., Chem. Commun., 1993, no. 9, pp. 774–776.
Yavorsky, P.M. and Gorin, E., J. Am. Chem. Soc., 1962, vol. 84, no. 6, pp. 1071–1072.
Werner, T.F. and Olsson, L.-I., J. Label. Compd. Radio-pharm., 1987, vol. 24, no. 1, pp. 29–39.
Tanga, M.J., Bupp, J.E., and Bradford, W.W., J. Label. Compd. Radiopharm., 2001, vol. 44, no. 6, pp. 405–411.
Leppala, E. and Wahala, K., J. Label. Compd. Radio-pharm., 2004, vol. 47, no. 1, pp. 25–30.
Characterisation of Catalysts, Thomas, J.M. and Lambert, R.M., Eds., Chichester: Wiley, 1980.
Somorjai, G.A., Adv. Catal. Res., 1977, vol. 26, no. 1, pp. 1–68.
Saito, K., Nakamura, A., Takey, H., and Wang, B., J. Am. Chem. Soc., 1980, vol. 112, no. 1, pp. 58–63.
Myasoedov, N.F., Sidorov, G.V., Kramerov, V.N., and Mishin, V.I., J. Label. Compd. Radiopharm., 1999, vol. 42, no. 9, pp. 859–866.
Myasoedov, N.F., J. Label. Compd. Radiopharm., 2007, vol. 50, nos. 9–10, pp. 831–847.
Kramerov, V.N., Catalytic methods for introducing tritium label into steroid hormones, Cand. Sci. (Chem.) Dissertation, Leningrad: State Inst. of Applied Chemistry, 1987.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 1998, vol. 40, no. 1, pp. 83–87.
Shevchenko, V.P., Nagaev, I.Yu., Potapova, A.V., and Myasoedov, N.F., Radiochemistry, 1998, vol. 40, no. 1, pp. 74–78.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 1999, vol. 41, no. 6, pp. 572–573.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 1999, vol. 41, no. 1, pp. 85–88.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 2012, vol. 54, no. 1, pp. 83–90.
Shevchenko, V.P., Nagaev, I.Yu., Myasoedov, N.F., and Susan, A., Abstracts of Papers, Sixth Int. Symp. “The Synthesis and Applications of Isotopes and Isotopically Labeled Compounds (ISSAIILC6),” Philadelphia, Pennsylvania, 1997, p. 73.
Hanzlik, R.P., Wiley, R.A., and Gillesse, T.J., J. Label. Compd. Radiopharm., 1979, vol. 16, no. 4, pp. 523–529.
Magatti, C.V., Hesk, D., Lauzon, M.J., et al., J. Label. Compd. Radiopharm., 1998, vol. 41, no. 8, pp. 731–739.
Kingston, L.P., Lockley, W.J.S., Mather, A.N., and Wilkinson, D.J., Synthesis and Applications of Isotopically Labeled Compounds, Pleiss U. and Voges, R., Eds., Chichester: Wiley, 2001, vol. 7, pp. 105–108.
Kessar, S.V., Pure Appl. Chem., 1990, vol. 62, no. 7, pp. 1397–1400.
Brook, A.G., Acc. Chem. Res., 1974, vol. 7, no. 3, pp. 77–84.
Arns, S., Moreau, A., and Young, R.N., J. Label. Compd. Radiopharm., 2010, vol. 53, no. 4, pp. 205–207.
Andres, H., Abstracts of Papers, Seventh Int. Symp. “The Synthesis and Applications of Isotopes and Iso-topically Labelled Compounds,” Dresden (Germany), 2000, p. 29.
Hong, Y., Bonacorsi, S.J., Jr., Tian, Y., et al., J. Label. Compd. Radiopharm., 2008, vol. 51, no. 2, pp. 113–117.
Voges, R., Heys, J.R., and Moenius, T., Preparation of Compounds Labeled with Tritium and Carbon-14, Wiley, 2009.
Bartok, M. and Czombos, J., Stereochemistry of Heterogeneous Metal Catalysis, Chichester: Wiley, 1985.
Sedlacek, J. and Wells, P.B., Adv. Catal., 1973, vol. 23, no. 1, pp. 123–155.
Ioffe, I.I., Reshetov, V.A., and Dobrotvorskii, A.M., Geterogennyi kataliz (Heterogeneous Catalysis), Leningrad: Khimiya, 1985.
Balandin, A.A., Sovremennoe sostoyanie teorii getero-gennogo kataliza (State-of-the-Art of the Theory of Heterogeneous Catalysis), Moscow: Nauka, 1968.
Pichat, L., The Synthesis and Applications of Isotopically Labeled Compounds: Proc. Second Int. Symp., Muccino, R.R., Ed., Kansas City, MO, 1985, pp. 133–138.
Sokol’skii, D.V., Optimal’nye katalizatory gidriro-vaniya v rastvorakh (Optimum Catalysts for Hydrogenation in Solutions), Alma-Ata: Nauka Kaz. SSR, 1970.
Sokol’skii, D.V., Gidrirovanie v rastvorakh (Hydrogenation in Solutions), Alma-Ata: Nauka, 1979.
Shopov, D. and Andreev, A., Khimicheskaya svyaz’ pri adsorbtsii i katalize. I. Metally (Chemical Bond in Adsorption and Catalysis. I. Metals), Sofia: Bolg. Akad. Nauk, 1975.
Popova, N.M., Babenkova, L.V., and Savel’eva, G.A., Adsorbtsiya i vzaimosvyaz’ prosteishikh gazov s metallami VIII gruppy (Adsorption and Interconnection of the Simplest Gases with Group VIII Metals), Alma-Ata: Nauka, 1979.
Charlot, M.-F. and Kahn, O., Surf. Sci., 1979, vol. 81, no. 1, pp. 90–108.
Lauher, J.W., J. Am. Chem. Soc., 1979, vol. 101, no. 10, pp. 2604–2607.
Gel’d, P.V. and Ryabov, R.A., Vodorod v metallakh (Hydrogen in Metals), Moscow: Metallurgiya, 1974.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Pharm. Chem. J., 1999, T. 33, N 6, pp. 299–312.
Shevchenko, V.P. and Myasoedov, N.F., Isotopes in the Physical and Biochemical Sciences, vol. 1: Labelled Compounds, part A. Buncel, E. and Jones, J.R., Eds., New York: Elsevier, 1987, pp. 237–287.
Shevchenko, V.P. and Myasoedov, N.F., Isotopes in the Physical and Biochemical Sciences, vol. 1: Labelled Compounds, part B, Buncel, E. and Jones, J.R., Eds., New York: Elsevier, 1991, pp. 179–231.
Shevchenko, V.P., Myasoedov, N.F., Bezuglov, V.V. and Bergel’son, L.D., Khim. Prirodn. Soedin., 1980, no. 2, pp. 148–157.
Sadovskaya, V.L., Rakitin, L.Yu., Grishina, I.I., et al., Bioorg. Khim., 1990, vol. 16, no. 10, pp. 1407–1412.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Russ. Chem. Rev., 1999, vol. 68, no. 10, pp. 859–879.
McQuillin, F.J., Homogeneous Hydrogenation in Organic Chemistry, Springer, 1976.
Kalinin, V.N., Mel’ nik, O.A., Sakharova, A.A., et al., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985. vol. 34, no. 11, pp. 2258–2263.
Lockley, W.J.S., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 5–6, pp. 227–230.
Zaera, F., Catal. Lett., 2003, vol. 91, nos. 1–2, pp. 1–10.
Brandt, B., Fischer, J.-H., Ludwig, W., et al., J. Phys. Chem. C, 2008, vol. 112, no. 30, pp. 11408–11420.
Doyle, A.M., Shaikhutdinov, Sh.K., and Freund, H.-J., J. Catal., 2004, vol. 223, pp. 444–453.
Brundish, D.E., Combe, M.G., and Wade, R., J. Label. Compd. Radiopharm., 1983, vol. 20, no. 7, pp. 869–886.
Long, M.A., Morimoto, H., and Williams, P.G., J. Label. Compd. Radiopharm., 1995, vol. 36, no. 11, pp. 1037–1049.
Chappelle, M.R. and Morgan, A.D., J. Label. Compd. Radiopharm., 2004, vol. 47, no. 5, p. 317.
Petros, R.A. and Shah, J., J. Label. Compd. Radio-pharm., 2014, vol. 57, no. 1, pp. 53–56.
Nagaev, I.Yu., Shevchenko, V.P., and Myasoedov, N.F., Radiochemistry, 1999, vol. 41, no. 4, pp. 305–317.
Shevchenko, V.P., Synthesis and study of isotopically modified lipids and their analogs, Doctoral (Chem.) Dissertation, Moscow: Inst. of Molecular Genetics, Russian Acad. Sci., 1992.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiokhimiya, 1993, vol. 35, no. 4, pp. 106–109.
Shevchenko, V.P., Faradzheva, S.V., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 1998, vol. 40, no. 1, pp. 88–92.
Shevchenko, V.P., Nagaev, I.Yu., Potapova, A.V., and Myasoedov, N.F., Radiokhimiya, 1995, vol. 37, no. 3, pp. 265–269.
Rozanov, V.V. and Krylov, O.V., Russ. Chem. Rev., 1997, vol. 66, no. 2, pp. 107–120.
Prins, R., Chem. Rev., 2012, vol. 112, no. 5, pp. 2714–2738.
Prins, R., Palfi, V.K., and Reiher, M., J. Phys. Chem. C, 2012, vol. 116, no. 27, pp. 14274–14283.
Bell, R.P., The Tunnel Effect in Chemistry, London: Chapman and Hall, 1980.
Compton, R.G., Electron Tunneling in Chemistry, vol. 30 of Comprehensive Chemical Kinetics, New York: Elsevier, 1989.
Prasittichai, C., Avila, J.R., Farha, O.K., and Hupp, J.T., J. Am. Chem. Soc., 2013, vol. 135, no. 44, pp. 16328–16331.
De Keczer, S.A., Lane, T.S., Voronin, T., and Masjedizadeh, M.R., J. Label. Compd. Radiopharm., 2005, vol. 48, no. 14, pp. 1013–1023.
Archer, W.J., Cook, R., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1983, no. 6, pp. 813–819.
Ciszewska, G., Pfefferkorn, H., Tang, Y.S., et al., J. Label. Compd. Radiopharm., 1997, vol. 39, no. 8, pp. 651–668.
Henot, F., Thellend, A., Pillon, F., et al., J. Label. Compd. Radiopharm., 1996, vol. 38, no. 6, pp. 579–583.
Scheigetz, J., Berthelette, C., Li, C., and Zamboni, R.J., J. Label. Compd. Radiopharm., 2004, vol. 47, no. 12, pp. 881–889.
Pajak, M. and Kanska, M., J. Label. Compd. Radio-pharm., 2006, vol. 49, no. 12, pp. 1061–1067.
Borisov, Yu.A. and Zolotarev, Yu.A., Russ. J. Phys. Chem. A, 2002, vol. 76. no. 4, pp. 635–639.
Somorjai, G.A., Chemistry in Two Dimensions. Surfaces, Ithaca: Cornell Univ. Press, 1981.
Lockley, W.J.S. and Hesk, D., J. Label. Compd. Ra-diopharm., 2010, vol. 53, nos. 11–12, pp. 704–715.
Sajiki, H., Hattori, K., Aoki, F., et al., Synlett, 2002, vol. 2002, no. 7, pp. 1149–1151.
Sajiki, H., Aoki, F., Esaki, H., et al., Org. Lett., 2004, vol. 6, no. 9, pp. 1485–1487.
Esaki, H., Ito, N., Sakai, Sh., et al., Tetrahedron, 2006, vol. 62, no. 47, pp. 10954–10961.
Maegawa, T., Fujiwara, Y., Inagaki, Y., et al., Angew. Chem. Int. Ed., 2008, vol. 47, no. 29, pp. 5394–5397.
Heys, J.R., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 716–721.
Hesk, D., Borges, S., Dumpit, R., et al., J. Label. Compd. Radiopharm., 2015, vol. 58, no. 2, pp. 36–41.
Hesk, D., Lavey, C.F., and McNamara, P., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 722–730.
Filer, C.N., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 739–744.
Modutlwa, N., Maegawa, T., Monguchi, Y., and Sajiki, H., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 686–692.
Nekrasova, Yu.N., Zolotarev, Yu.A., and Navolotskaya, E.V., Biochemistry (Moscow), 2011, vol. 76, no. 12, pp. 1337–1341.
Rhee, S.-W., Ryan, K.J., and Tanga, M.J., J. Label. Compd. Radiopharm., 2011, vol. 54, no. 7, pp. 367–370.
Filer, C.N., J. Label. Compd. Radiopharm., 2017, vol. 60, no. 2, pp. 96–109.
Myasoedov, N.F., J. Label. Compd. Radiopharm., 1993, vol. 33, no. 5, pp. 391–401.
Shevchenko, V.P. and Myasoedov, N.F., J. Label. Compd. Radiopharm., 1982, vol. 19, no. 1, pp. 95–109.
Shevchenko, V.P., Myasoedov, N.F., and Bergel’son, L.D., Bioorg. Khim., 1979, vol. 5, no. 5, pp. 730–734.
Shevchenko, V.P., Nagayev, I.Yu., and Myasoedov, N.F., J. Label. Compd. Radiopharm., 1989, vol. 27, no. 10, pp. 1195–1214.
Huda, A.P.J., Tritium Labelling of Phospholipids Applied in Lecithin Aggregates, Univ. of Copenhagen, Faculty of Life Sciences, 2009.
Ho, J.Z., Zhang, A.S., Tang, Y.S., et al., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 5–6, pp. 433–435.
Shevchenko, V.P., Nagaev, I.Yu., Myasoedov, N.F., et al., Radiochemistry, 2000, vol. 42, no. 2, pp. 191–195.
Shevchenko, V.P., Nagaev, I.Yu., Potapova, A.V., and Myasoedov, N.F., Radiokhimiya, 1994, vol. 36, no. 5, pp. 445–449.
Weygand–Hilgetag, Organisch-chemische Experimentierkunst, Leipzig Barth, 1964, 3rd ed.
Andre, T. and Ullberg, S., J. Am. Chem. Soc., 1957, vol. 79, no. 2, pp. 494–495.
Gut, M. and Uskovic, M., J. Org. Chem., 1962, vol. 25, no. 5, pp. 792–796.
Elbert, T., Patil, M.R., and Marek, A., J. Label. Compd. Radiopharm., 2017, vol. 60, no. 3, pp. 176–182.
Marek, A., Klepetarova, B., and Elbert, T., Tetrahedron, 2015, vol. 71, no. 29, pp. 4874–4882.
Allen, P., Bragg, R.A., Caffrey, M., et al., J. Label. Compd. Radiopharm., 2017, vol. 60, no. 2, pp. 124–129.
Hickey, M.J., Allen, P.H., Caffrey, M., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 11, pp. 432–438.
Bertrand, R., Hamp, I., Bronstrup, M., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 14, pp. 604–610.
Tang, Y.S., Liu, W., Braun, M.P., and Ho, J.Z., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 5–6, pp. 441–442.
Christensen, J., Natt, F., Hunziker, J., et al., J. Label. Compd. Radiopharm., 2012, vol. 55, no. 6, pp. 189–196.
Rauh, J.J., Lahm, G.P., Pahutski, T.F., et al., J. Label. Compd. Radiopharm., 2010, vol. 53, no. 1, pp. 51–52.
Malmquist, J., Bernlind, A., Johansson, M., et al., J. Label. Compd. Radiopharm., 2012, vol. 55, no. 10, pp. 393–399.
Lamb, P.B., McElhinny, C.J., Sninski, T., et al., J. Label. Compd. Radiopharm., 2009, vol. 52, no. 11, pp. 457–462.
Allen, P., Coissard, V., Wilkinson, D.J., et al., J. Label. Compd. Radiopharm., 2009, vol. 52, no. 6, pp. 214–215.
Damont, A., Garcia-Argote, S., Buisson, D.-A., et al., J. Label. Compd. Radiopharm., 2015, vol. 58, no. 1, pp. 1–6.
Postolache, C. and Matei, L., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 5–6, pp. 459–461.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 2002, vol. 44, no. 4, pp. 380–383.
Shevchenko, V.P., Nagaev, I.Yu., Myasoedov, N.F., et al., Russ. J. Bioorg. Chem., 2002, vol. 28, no. 3, pp. 231–233.
Bragg, R.A., Bushby, N., Ericsson, C., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 11, pp. 454–461.
Boykin, D.W., Jr., Patel, A.R., and Lutz, R.E., J. Med. Chem., 1968, vol. 11, no. 2, pp. 273–277.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Radiochemistry, 2002, vol. 44, no. 1, pp. 75–80.
Cerny, B., Jegorov, A., Polivkova, J., et al., J. Label. Compd. Radiopharm., 1998, vol. 41, no. 4, pp. 267–272.
Tang, Y.S. and Ho, J.Z., J. Label. Compd. Radio-pharm., 2010, vol. 53, nos. 5–6, pp. 437–440.
Lavey, C.F., Hesk, D., Borges, S., et al., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 5–6, pp. 368–371.
Shu, A.Y.L. and Heys, J.R., Proc. Sixth Int. Symp. “The Synthesis and Applications of Isotopes and Isotopically Labeled Compounds (ISSAIILC6),” Heys, J.R. and Melillo, D.G., Eds., Philadelphia, Pennsylvania, 1997, pp. 223–226.
Devlin, J., Kerr, W.J., Lindsay, D.M., et al., Molecules, 2015, vol. 20, no. 7, pp. 11676–11698.
Kerr, W.J., Reid, M., and Tuttle, T., ACS Catal., 2015, vol. 5, no. 1, pp. 402–410.
Kerr, W.J., Mudd, R.J., Owens, P.K., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 14, pp. 601–603.
Lockley, W.J.S., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 668–673.
Nilsson, G.N. and Kerr, W.J., J. Label. Compd. Radio-pharm., 2010, vol. 53, nos. 11–12, pp. 662–667.
Simonsson, R., Stenhagen, G., Ericsson, C., and Elmore, C.S., J. Label. Compd. Radiopharm., 2013, vol. 56, no. 6, pp. 334–337.
Brown, J.A., Cochrane, A.R., Irvine, S., et al., Adv. Synth. Catal., 2014, vol. 356, no. 17, pp. 3551–3562.
Parmentier, M., Hartung, T., Pfaltz, A., and Muri, D., Chem. Eur. J., 2014, vol. 20, no. 36, pp. 11 496–11 504.
Herbert, J.M., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 658–661.
Marek, A., Pedersen, M.H.F., Vogensen, S.B., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 12, pp. 476–483.
Atzrodt, J., Derdau, V., Kerr, W.J., et al., Tetrahedron, 2015, vol. 71, no. 13, pp. 1924–1929.
Chappelle, M.R. and Hawes, C.R., J. Label. Compd. Radiopharm., 2010, vol. 53, nos. 11–12, pp. 745–751.
Neumann, K.T., Lindhardt, A.T., Bang-Andersen, B., and Skrydstrup, T., J. Label. Compd. Radiopharm., 2017, vol. 60, no. 1, pp. 30–35.
Lindelof, A., Ericsson, C., Simonsson, R., et al., J. Label. Compd. Radiopharm., 2016, vol. 59, no. 9, pp. 340–345.
Pieters, G., Taglang, C., Bonnefille, E., et al., Angew. Chem., 2014, vol. 126, no. 1, pp. 234–238.
Nath, B.K. and Ganguli, J.N., Asian J. Sci. Technol., 2014, vol. 5, no. 3, pp. 238–240.
Haack, K.-J., Hashiguchi, S., Fujii, A., et al., Angew. Chem. Int. Ed. Engl., 1997, vol. 36, pp. 285–288.
Yamakawa, M., Ito, H., and Noyori, R., J. Am. Chem. Soc., 2000, vol. 122, no. 7, pp. 1466–1478.
Murata, K., Okano, K., Miyagi, M., et al., Org. Lett., 1999, vol. 1, no. 7, pp. 1119–1121.
Hashiguchi, S., Fujii, A., Haack, K.-J., et al., Angew. Chem. Int. Ed. Engl., 1997, vol. 36, pp. 288–290.
Kanada, R.M. and Ogasawara, K., Chem. Commun., 1998, no. 16, pp. 1755–1756.
Hashiguchi, S., Fujii, A., Takehara, J., et al., J. Am. Chem. Soc., 1995, vol. 117, no. 28, pp. 7562–7563.
Fujii, A., Hashiguchi, S., Uematsu, N., et al., J. Am. Chem. Soc., 1996, vol. 118, no. 10, pp. 2521–2522.
Matsumura, K., Hashiguchi, S., Ikariya, T., and Noyori, R., J. Am. Chem. Soc., 1997, vol. 119, no. 37, pp. 8738–8739.
Okano, K., Murata, K., and Ikariya, T., Tetrahedron Lett., 2000, vol. 41, no. 48, pp. 9277–9280.
Koike, T., Murata, K., and Ikariya, T., Org. Lett., 2000, vol. 2, no. 24, pp. 3833–3836.
Noyori, R. and Hashiguchi, S., Acc. Chem. Res., 1997, vol. 30, no. 2, pp. 97–102.
Palmer, M.J. and Wills, M., Tetrahedron: Asymmetry, 1999, vol. 10, no. 11, pp. 2045–2061.
Uematsu, N., Fujii, A., Hashiguchi, S., et al., J. Am. Chem. Soc., 1996, vol. 118, no. 20, pp. 4916–4917.
Soni, R., Cheung, F.K., Clarkson, G.C., et al., Org. Biomol. Chem., 2011, no. 9, pp. 3290–3294.
Shevchenko, V.P., Nagaev, I.Yu., and Myasoedov, N.F., Russ. Chem. Rev., 2003, vol. 72, no. 5, pp. 423–446.
Author information
Authors and Affiliations
Additional information
Russian Text © The Author(s), 2019, published in Radiokhimiya, 2019, Vol. 61, No. 3, pp. 183–216.
Rights and permissions
About this article
Cite this article
Shevchenko, V.P., Nagaev, I.Y. & Myasoedov, N.F. Effect of Processes Occurring in the Presence of Metal Catalysts on the Main Characteristics of the Hydrogen Isotope Labeled Organic Compounds Obtained. Radiochemistry 61, 257–292 (2019). https://doi.org/10.1134/S1066362219030019
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1066362219030019