Advertisement

Russian Chemical Bulletin

, Volume 65, Issue 2, pp 445–450 | Cite as

Direct functionalization of the C—H bond in (hetero)arenes: aerobic photoinduced oxidative coupling of azines with aromatic nucleophiles (SN H-reactions) in the presence of a CdS/TiO2 photocatalyst

  • I. A. Utepova
  • O. N. Chupakhin
  • M. A. Trestsova
  • A. A. Musikhina
  • D. A. Kucheryavaya
  • V. N. Charushin
  • A. A. Rempel
  • N. S. Kozhevnikova
  • A. A. Valeeva
  • A. I. Mikhaleva
  • B. A. Trofimov
Full Articles

Abstract

A highly selective coupling of azines with aromatic nucleophiles (SN H-reactions) in the presence of a heterogeneous oxidation system O2/CdS/TiO2 upon exposure to daylight was accomplished.

Key words

SNH-reactions C—H functionalization azines aerobic photooxidation TiO2 CdS/TiO2 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    I. P. Beletskaya, V. P. Ananikov, Russ. J. Org. Chem. (Engl. Transl.), 2015, 51, 145 [Zh. Org. Khim., 2015, 51, 159].CrossRefGoogle Scholar
  2. 2.
    V. P. Ananikov, L. L. Khemchyan, Y. V. Ivanova, V. I. Bukhtiyarov, A. M. Sorokin, I. P. Prosvirin, S. Z. Vatsadze, A. V. Medved´ko, V. N. Nuriev, A. D. Dilman, V. V. Levin, I. V. Koptyug, K. V. Kovtunov, V. V. Zhivonitko, V. A. Likholobov, A. V. Romanenko, P. A. Simonov, V. G. Nenajdenko, O. I. Shmatova, V. M. Muzalevskiy, M. S. Nechaev, A. F. Asachenko, O. S. Morozov, P. B. Dzhevakov, S. N. Osipov, D. V. Vorobyeva, M. A. Topchiy, M. A. Zotova, S. A. Ponomarenko, O. V. Borshchev, Y. N. Luponosov, A. A. Rempel, A. A. Valeeva, A. Y. Stakheev, O. V. Turova, I. S. Mashkovsky, S. V. Sysolyatin, V. V. Malykhin, G. A. Bukhtiyarova, A. O. Terent´ev, I. B. Krylov, Russ. Chem. Rev. (Engl. Transl.), 2014, 83, 885.CrossRefGoogle Scholar
  3. 3.
    H. M. L. Davies, D. Morton, Angew. Chem. Int. Ed., 2014, 53, 10256.CrossRefGoogle Scholar
  4. 4.
    D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc., 2007, 129, 12072.CrossRefGoogle Scholar
  5. 5.
    G. Brasche, J. Garcha-Fortanet, S. L. Buchwald, Org. Lett., 2008, 10, 2207.CrossRefGoogle Scholar
  6. 6.
    Y. Gu, D. Wang, Tetrahedron Lett., 2010, 51, 2004.CrossRefGoogle Scholar
  7. 7.
    S. Potavathri, K. C. Pereira, S. I. Gorelsky, A. Pike, A. P. LeBris, B. DeBoef, J. Am. Chem. Soc., 2010, 132, 14676.CrossRefGoogle Scholar
  8. 8.
    J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem., Int. Ed., 2012, 51, 8960.CrossRefGoogle Scholar
  9. 9.
    O. N. Chupakhin, V. N. Charushin, H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York—San Diego, 1994, 367 pp.Google Scholar
  10. 10.
    Metal Free C-H Functionalisation of Aromatics. Nucleophilic Displacement of Hydrogen, Eds V. N. Charushin, O. N. Chupakhin, in Topics in Heterocyclic Chemistry, Eds B. U. W. Maes, J. Cossy, S. Polanic, Springer, Switzerland, 2014, 37, 283 pp.Google Scholar
  11. 11.
    V. N. Charushin, O. N. Chupakhin, Pure Appl. Chem., 2004, 76, 1621.CrossRefGoogle Scholar
  12. 12.
    M. Mąkosza, Chem. Soc. Rev., 2010, 39, 2855.CrossRefGoogle Scholar
  13. 13.
    M. Mąkosza, Synthesis, 2011, 15, 2341.CrossRefGoogle Scholar
  14. 14.
    V. F. Traven´, Organicheskaya khimiya [Organic Chemistry], Binom. Laboratoriya znanii, Moscow, 2013, V. 3, 388 pp. (in Russian).Google Scholar
  15. 15.
    M. B. Smith, J. March, March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, J. Wiley and Sons, Hoboken, NJ, 2007, 2384 pp.Google Scholar
  16. 16.
    J. Joule, K. Mills, Chemistry of Heterocyclic Compounds, Transl. from English by. F. V. Zaitseva and A. V. Karchava, Ed. M. A. Yurovskaya, Mir, Moscow, 2004, 728 pp.Google Scholar
  17. 17.
    O. N. Chupakhin, I. A. Utepova, I. S. Kovalev, V. L. Rusinov, Z. A. Starikova, Eur. J. Org. Chem., 2007, 5, 857.CrossRefGoogle Scholar
  18. 18.
    M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin, J. Org. Chem., 2012, 77, 9087.CrossRefGoogle Scholar
  19. 19.
    I. A. Utepova, A. A. Musikhina, O. N. Chupakhin, P. A. Slepukhin, Organometallics, 2011, 30, 3047.CrossRefGoogle Scholar
  20. 20.
    I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushina, A. A. Rempel, Green Chem., 2015, 17, 4401.CrossRefGoogle Scholar
  21. 21.
    T. Caronna, C. Gambarotti, L. Palmisano, C. Punta, M. Pierini, F. Recupero, J. Photochem. Photobiol. A, 2007, 189, 322.CrossRefGoogle Scholar
  22. 22.
    D. Zhang, G. Li, X. Yang, J. C. Yu, Chem. Commun., 2009, 29, 4381.CrossRefGoogle Scholar
  23. 23.
    E. A. Kozlova, N. S. Kozhevnikova, S. V. Cherepanova, T. P. Lyubina, E. Yu. Gerasimov, V. V. Kaichev, A. V. Vorontsov, S. V. Tsybulya, A. A. Rempel, V. N. Parmon, J. Photochem. Photobiol. A, 2012, 250, 103.CrossRefGoogle Scholar
  24. 24.
    A. A. Rempel, E. A. Kozlova, T. I. Gorbunova, S. V. Cherepanova, E. Yu. Gerasimov, N. S. Kozhevnikova, A. A. Valeeva, E. Yu. Korovin, V. V. Kaichev, Yu. A. Shchipunov. Catalysis Communication, 2015, 68, 61.CrossRefGoogle Scholar
  25. 25.
    J. C. Kim, J. Choi, Y. B. Lee, J. H. Hong, J. I. Lee, J. W. Yang, W. I. Lee, N. H. Hur, Chem. Commun., 2006, 48, 5024.CrossRefGoogle Scholar
  26. 26.
    J. S. Jang, S. M. Ji, S. W. Bae, H. C. Son, J. S. Lee, J. Photochem. Photobiol. A, 2007, 188, 112.CrossRefGoogle Scholar
  27. 27.
    W.-T. Sun, Y. Yu, H.-Y. Pan, X.-F. Gao, Q. Chen, L.-M. Peng, J. Am. Chem. Soc., 2008, 130, 1124.CrossRefGoogle Scholar
  28. 28.
    S. Banerjee, S. K. Mohapatra, P. P. Das, M. Misra, Chem. Mater., 2008, 20, 6784.CrossRefGoogle Scholar
  29. 29.
    B. A. Trofimov, A. I. Mikhaleva, E. Yu. Schmidt, A. M. Vasil´tsov, A. V. Ivanov, N. I. Protsuk, O. A. Ryapolov, Dokl. Chem. (Engl. Transl.), 2010, 435, 307 [Dokl. Akad. Nauk, 2010, 435, 60].Google Scholar
  30. 30.
    B. A. Trofimov, A. I. Mikhaleva, E. Yu. Shmidt, L. N. Sobenina, Chemistry of Pyrroles, CRC Press, Florida, 2014, 398 pp.Google Scholar
  31. 31.
    A. I. Mikhaleva, O. V. Petrova, L. N. Sobenina, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 47, 1367 [Khim. Geterotsikl. Soedin., 2011, 47, 1649].CrossRefGoogle Scholar
  32. 32.
    E. N. Nelin, A. K. Sheinkman, A. I. Mikhaleva, B. A. Trofimov, Chem. Heterocycl. Compd. (Engl. Transl.), 1978, 14, 127 [Khim. Geterotsikl. Soedin., 1978, 167].CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • I. A. Utepova
    • 1
    • 2
  • O. N. Chupakhin
    • 1
    • 2
  • M. A. Trestsova
    • 1
  • A. A. Musikhina
    • 1
  • D. A. Kucheryavaya
    • 1
  • V. N. Charushin
    • 1
    • 2
  • A. A. Rempel
    • 1
    • 3
  • N. S. Kozhevnikova
    • 3
  • A. A. Valeeva
    • 1
    • 3
  • A. I. Mikhaleva
    • 4
  • B. A. Trofimov
    • 4
  1. 1.Ural Federal UniversityEkaterinburgRussian Federation
  2. 2.I. Ya. Postovsky Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation
  3. 3.Institute of Solid State ChemistryUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation
  4. 4.A. E. Favorsky Irkutsk Institute of ChemistrySiberian Branch of the Russian Academy of SciencesIrkutskRussian Federation

Personalised recommendations