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Arylation of Adamantanamines: XI. Comparison of the Catalytic Efficiency of Palladium and Copper Complexes in Reactions of Adamantanamines with Fluorinated 2-Bromopyridines

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Abstract

A comparative study of the catalytic efficiency of Pd(0) and Cu(I) complexes in the reactions of adamantanamines with fluoro- and trifluoromethyl-substituted 2-bromopyridines was carried out using previously optimized catalytic systems. It was shown that in the absence of steric hindrances in the starting compounds, the copper and palladium catalysts were comparable in efficiency. In some cases, the yields of the target N-heteroarylated compounds in the copper-catalyzed reactions were even higher, which can be explained by the formation of N,N-diheteroarylated by-products under palladium-catalyzed conditions. At the same time, ortho-fluorine- and ortho-trifluoromethyl-substituted 2-bromopyridines successfully react exclusively under palladium catalysis.

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REFERENCES

  1. Lyakhovich, M.S., Murashkina, A.V., Averin, A.D., Abel, A.S., Maloshitskaya, O.A., Savelyev, E.N., Orlinson, B.S., and Beletskaya, I.P., Russ. J. Org. Chem., 2019, vol. 55, p. 737. https://doi.org/10.1134/S1070428019060010

    Article  CAS  Google Scholar 

  2. Gillis, E.P., Eastman, K.J., Hill, M.D., Donnelly, J.D., and Meanwell, N.A., J. Med. Chem., 2015, vol. 58, p. 8315. https://doi.org/10.1021/acs.jmedchem.5b00258

    Article  CAS  PubMed  Google Scholar 

  3. Swallow, S., Prog. Med. Chem., 2015, vol. 54, p. 65. https://doi.org/10.1016/bs.pmch.2014.11.001

    Article  PubMed  Google Scholar 

  4. Knight, D., Curr. Opin. Investig. Drugs, 2004, vol. 5, p. 557.

    CAS  PubMed  Google Scholar 

  5. Kang, S., Min, H.-J., Kang, M.-S., Jung, M.-G., and Kim, S., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 1748. https://doi.org/10.1016/j.bmcl.2013.01.055

    Article  CAS  PubMed  Google Scholar 

  6. Nenajdenko, V.G., Muzalevskiy, V.M., and Shastin, A.V., Chem. Rev., 2015, vol. 115, p. 973. https://doi.org/10.1021/cr500465n

    Article  CAS  PubMed  Google Scholar 

  7. 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., Nenajdenko, 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., Dil’man, 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, p. 425. https://doi.org/10.1070/RCR4871

    Article  CAS  Google Scholar 

  8. Hutchinson, J.H., Rowbottom, M.W., Lonergan, D., Darlington, J., Prodanovich, P., King, C.D., Evans, J.F., and Bain, G., ACS Med. Chem. Lett., 2017, vol. 8, p. 423. https://doi.org/10.1021/acsmedchemlett.7b00014

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Evecen, M., Kara, M., Idil, O., and Tanak, H., J. Mol. Struct., 2017, vol. 1137, p. 206. https://doi.org/10.1016/j.molstruc.2017.02.060

    Article  CAS  Google Scholar 

  10. Kivitz, A.J., Gutierrez-Ureña, S.R., Poiley, J., Genovese, M.C., Kristy, R., Shay, K., Wang, X., Garg, J.P., and Zubrzycka-Sienkiewicz, A., Arthritis Rheumatol., 2017, vol. 69, p. 709. https://doi.org/10.1002/art.39955

    Article  CAS  PubMed  Google Scholar 

  11. Leovac, V.M., Rodić, M.V., Jovanović, L.S., Joksović, M.D., Stanojković, T., Vujčić, M., Sladić, D., Marković, V., and Vojinović-Ješić, L.S., Eur. J. Inorg. Chem., 2015, vol. 2015, p. 882. https://doi.org/10.1002/ejic.201403050

    Article  CAS  Google Scholar 

  12. Liu, S., Qian, P., Wan, F.-X., Shi, Y.-H., and Jiang, L., J. Chin. Chem. Soc., 2019, vol. 66, p. 330. https://doi.org/10.1002/jccs.201800259

    Article  CAS  Google Scholar 

  13. Ryu, J.H., Kim, S., Han, H.Y., Son, H.J., Lee, H.J., Shin, Y.A., Kim, J.-S., and Park, H.-g., Bioorg. Med. Chem. Lett., 2015, vol. 25, p. 695. https://doi.org/10.1016/j.bmcl.2014.11.074

    Article  CAS  PubMed  Google Scholar 

  14. Rohde, J.J., Pliushchev, M.A., Sorensen, B.K., Wodka, D., Shuai, Q., Wang, J., Fung, S., Monzon, K.M., Chiou, W.J., Pan, L., Deng, X., Chovan, L.E., Ramaiya, A., Mullally, M., Henry, R.F., Stolarik, D.F., Imade, H.M., Marsh, K.C., Beno, D.W.A., Fey, T.A., Droz, B.A., Brune, M.E., Camp, H.S., Sham, H.L., Frevert, E.U., Jacobson, P.B., and Link, J.T., J. Med. Chem., 2007, vol. 50, p. 149. https://doi.org/10.1021/jm0609364

    Article  CAS  PubMed  Google Scholar 

  15. Sorensen, B., Rohde, J., Wang, J., Fung, S., Monzon, K., Chiou, W., Pan, L., Deng, X., Stolarik, D., Frevert, E.U., Jacobson, P., and Link, J.T., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5958. https://doi.org/10.1016/j.bmcl.2006.08.129

    Article  CAS  PubMed  Google Scholar 

  16. Collins, K.C. and Janda, K.D., Bioconjugate Chem., 2014, vol. 25, p. 593. https://doi.org/10.1021/bc500016k

    Article  CAS  Google Scholar 

  17. Sambiagio, C., Marsden, S.P., Blacker, A.J., and McGowan, P.C., Chem. Soc. Rev., 2014, vol. 43, p. 3525. https://doi.org/10.1039/C3CS60289C

    Article  CAS  PubMed  Google Scholar 

  18. Okano, K., Tokuyama, H., and Fukuyama, T., Chem. Commun., 2014, vol. 50, p. 13650. https://doi.org/10.1039/C4CC03895A

    Article  CAS  Google Scholar 

  19. Junge, K., Wienhöfer, G., Beller, M., Tlili, A., Evano, G., Taillefer, M., Kempe, R., Malbertz, C., Klankermayer, J., Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Three Volumes, 3rd, Edn. Cornils, B., Herrmann, W.A., Beller, M., and Paciello, R., Eds., Hoboken: John Wiley & Sons, Inc. 2017, p. 691. https://doi.org/10.1002/9783527651733.ch10

  20. Shaughnessy, K.H., Ciganek, E., De Vasher, R.B., and Denmark, S.E., Copper-Catalyzed Amination of Aryl and Alkenyl Electrophiles, Hoboken: John Wiley & Sons, Inc., 2017.

  21. Neetha, M., Saranya, S., Ann Harry, N., and Anilkumar, G., ChemistrySelect, 2020, vol. 5, p. 736. https://doi.org/10.1002/slct.201904436

    Article  CAS  Google Scholar 

  22. Abel, A.S., Averin, A.D., Buryak, A.K., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Synthesis, 2017, vol. 49, p. 5067. https://doi.org/10.1055/s-0036-1590860

    Article  CAS  Google Scholar 

  23. Abel, A.S., Kotovshchikov, Y.N., Averin, A.D., Maloshitskaya, O.A., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Heterocycles, 2019, vol. 99, p. 1342. https://doi.org/10.3987/COM-18-S(F)64

    Article  Google Scholar 

  24. Lyakhovich, M.S., Averin, A.D., Grigorova, O.K., Roznyatovsky, V.A., Maloshitskaya, O.A., and Beletskaya, I.P., Molecules, 2020, vol. 25, p. 1084. https://doi.org/10.3390/molecules25051084

    Article  CAS  PubMed Central  Google Scholar 

  25. Averin, A.D., Ranyuk, E.R., Golub, S.L., Buryak, A.K., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Synthesis, 2007, vol. 2007, p. 2215. https://doi.org/10.1055/s-2007-983760

    Article  CAS  Google Scholar 

  26. Novikov, S.S., Khardin, A.P., Radchenko, S.S., Novakov, I.A., Orlinson, B.S., Blinov, V.F., Gorelov, V.I., and Zamakh, V.I., USSR Patent no. 682507, 1978; Chem. Abstr., 1979, vol. 91, no. P193887e.

  27. Novakov, I.A., Kulev, I.A., Radchenko, S.S., Birznieks, K.A., Boreko, E.I., Vladyko, G.V., and Korobchenko, L.V., Pharm. Chem. J., 1987, vol. 21, p. 287. https://doi.org/10.1007/BF00767400

    Article  Google Scholar 

  28. Popov, Yu.V., Mokhov, V.M., and Tankabekyan, N.A., Russ. J. Appl. Chem., 2013, vol. 86, p. 404. https://doi.org/10.1134/S1070427213030191

    Article  CAS  Google Scholar 

  29. Novakov, I.A., Orlinson, B.S., Savel’ev, E.N., Potaenkova, E.A., and Shilin, A.K., RF Patent no. RU 2495020 C1, 2013.

  30. Ukai, T., Kawazura, H., Ishii, Y., Bonnet, J.J., and Ibers, J.A., J. Organomet. Chem., 1974, vol. 65, p. 253. https://doi.org/10.1016/S0022-328X(00)91277-4

    Article  CAS  Google Scholar 

  31. Abel, A.S., Averin, A.D., Anokhin, M.V., Maloshitskaya, O.A., Butov, G.M., Savelyev, E.N., Orlinson, B.S., Novakov, I.A., and Beletskaya, I.P., Russ. J. Org. Chem., 2015, vol. 51, p. 301. https://doi.org/10.1134/S1070428015030021

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 17-03-00888).

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Authors and Affiliations

  1. Lomonosov Moscow State University, 119991, Moscow, Russia

    M. S. Lyakhovich, A. V. Murashkina, S. P. Panchenko, A. D. Averin, A. S. Abel, O. A. Maloshitskaya & I. P. Beletskaya

  2. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    A. D. Averin & I. P. Beletskaya

  3. Volgograd State Technical University, 400005, Volgograd, Russia

    E. N. Savelyev, B. S. Orlinson & I. A. Novakov

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  1. M. S. Lyakhovich
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Correspondence to A. D. Averin.

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Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 5, pp. 700–717 https://doi.org/10.31857/S0514749221050037.

To the 70th anniversary of Academician of the Russian Academy of Sciences V.N. Charushin

For communication X, see [1].

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Lyakhovich, M.S., Murashkina, A.V., Panchenko, S.P. et al. Arylation of Adamantanamines: XI. Comparison of the Catalytic Efficiency of Palladium and Copper Complexes in Reactions of Adamantanamines with Fluorinated 2-Bromopyridines. Russ J Org Chem 57, 768–783 (2021). https://doi.org/10.1134/S1070428021050031

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