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The synthesis and comparative characterization of three novel electroactive iminoboronates containing ferrocene

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Abstract

Along our way towards the advanced saccharide-sensitive probes, three novel electroactive iminoboronate regioisomers of [(ferrocenylimino)methyl]phenylboronic acid have been synthesized. The ortho, meta, and para regioisomers were characterized structurally by NMR, MS, FT-IR, UV/Vis and their electrochemical behavior in aqueous solution was studied using cyclic voltammetry. The obtained results confirmed different behavior of the ortho isomer due to an interaction of boronic acid moiety with the proximate imine group of the iminoferrocenyl residue.

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References

  1. James TD, Sandanayake KRAS, Iguchi R, Shinkai S (1995) J Am Chem Soc 117:8982

    Article  CAS  Google Scholar 

  2. Hall DG (2005) Boronic acids. Wiley-Blackwell, London

    Book  Google Scholar 

  3. James TD, Phillips MD, Shinkai S (2006) Boronic acids in saccharide recognition. RSC Publishing, London

    Google Scholar 

  4. Sun X, James TD (2015) Chem Rev 115:8001

    Article  CAS  Google Scholar 

  5. Ward CJ, Patel P, James TD (2002) J Chem Soc Perkin Trans 1:462

    Article  Google Scholar 

  6. Wu X, Li Z, Chen XX, Fossey JS, James TD, Jiang YB (2013) Chem Soc Rev 42:8032

    Article  CAS  Google Scholar 

  7. Štěpnička P (2008) Ferrocenes. Wiley-Blackwell, London

    Google Scholar 

  8. Lacina K, Skládal P (2011) Electrochim Acta 56:10246

    Article  CAS  Google Scholar 

  9. Lacina K, Novotný J, Moravec Z, Skládal P (2015) Electrochim Acta 153:280

    Article  CAS  Google Scholar 

  10. Anzai JI (2016) Mat Sci Eng C 67:737

    Article  CAS  Google Scholar 

  11. Egawa Y, Seki T, Takahashi S, Anzai JI (2011) Mat Sci Eng C 31:1267

    Article  Google Scholar 

  12. Ori A, Shinkai S (1995) J Chem Soc Chem Commun 1771

  13. Norrild JC, Sotofte I (2001) J Chem Soc Perkin Trans 2:727

    Article  Google Scholar 

  14. Arimori S, Ushiroda S, Peter LM, Jenkins ATA, James TD (2002) Chem Commun 2368

  15. Norrild JC, Sotofte I (2002) J Chem Soc Perkin Trans 2:303

    Article  Google Scholar 

  16. Lacina K, Konhefr M, Novotný J, Potěšil D, Zdráhal Z, Skládal P (2014) Tetrahedron Lett 55:3235

    Article  CAS  Google Scholar 

  17. Adamczyk-Wozniak A, Cyranski MK, Fraczak BT, Lewandowska A, Madura ID, Sporzynski A (2012) Tetrahedron 68:3761

    Article  CAS  Google Scholar 

  18. Larkin JD, Fossey JS, James TD, Brooks BR, Bock CW (2010) J Phys Chem A 114:12531

    Article  CAS  Google Scholar 

  19. French TC, Bruice TC (1964) Biochemistry 3:1589

    Article  CAS  Google Scholar 

  20. French TC, Auld DS, Bruice TC (1965) Biochemistry 4:77

    Article  CAS  Google Scholar 

  21. Iglesias AL, García JJ (2009) J Mol Catal A Chem 298:51

    Article  CAS  Google Scholar 

  22. Cano R, Yus M, Ramón DJ (2011) Tetrahedron 67:8079

    Article  CAS  Google Scholar 

  23. Zhao J, Davidson MG, Mahon MF, Kociok-Köhn G, James TD (2004) J Am Chem Soc 126:16179

    Article  CAS  Google Scholar 

  24. Togni A, Hayashi T (1995) Ferrocenes—homogeneous catalysis—organic synthesis—material science. Wiley-Blackwell, London

    Google Scholar 

  25. Nöth H, Wrackmeyer B (1978) Nuclear magnetic resonance spectroscopy of boron compounds. Springer Nature, Berlin

    Book  Google Scholar 

  26. Cal PMSD, Vicente JB, Pires E, Coelho AV, Veiros LF, Cordeiro C, Gois PMP (2012) J Am Chem Soc 134:10299

    Article  CAS  Google Scholar 

  27. Couturier M, Tucker JL, Andersen BM, Dubé P, Negri JT (2001) Org Lett 3:465

    Article  CAS  Google Scholar 

  28. Brieger G, Nestrick TJ (1974) Chem Rev 74:567

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research has been financially supported by the Masaryk University project MUNI/A/1265/2015—Support of biochemical research at MU, by the Ministry of Education, Youth and Sports of the Czech Republic under the project CEITEC 2020 (LQ1601) and by the Czech Science Foundation (Project P206/12/G014).

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Authors and Affiliations

  1. Department of Biochemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37, Brno, Czech Republic

    Martin Konhefr, Monika Skrutková Langmajerová, Zdeněk Glatz & Petr Skládal

  2. Central European Institute of Technology, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic

    Karel Lacina, Petr Skládal & Ctibor Mazal

  3. Department of Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37, Brno, Czech Republic

    Ctibor Mazal

Authors
  1. Martin Konhefr
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  2. Karel Lacina
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  3. Monika Skrutková Langmajerová
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  4. Zdeněk Glatz
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  5. Petr Skládal
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  6. Ctibor Mazal
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Corresponding author

Correspondence to Karel Lacina.

Electronic supplementary material

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706_2017_2028_MOESM1_ESM.pdf

Supplementary material 1 (PDF 3225 kb) Supplementary data (supplementary material includes 1H, 11B, 13C NMR, MS and FTIR spectra associated with this article) can be found in the online version

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Konhefr, M., Lacina, K., Langmajerová, M.S. et al. The synthesis and comparative characterization of three novel electroactive iminoboronates containing ferrocene. Monatsh Chem 148, 1953–1958 (2017). https://doi.org/10.1007/s00706-017-2028-3

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  • DOI: https://doi.org/10.1007/s00706-017-2028-3

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