Skip to main content
SpringerLink
Log in

Preparation of arylboronic and diarylborinic acids from potassium aryl(fluoro)borates

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

  • 1 Altmetric

Abstract

A series of acids ArB(OH)2 and Ar2BOH with an electron-withdrawing aryl group were obtained from the corresponding borates K[ArBF3] and K[Ar2BF2] by the action of MX3 (M = B, Al; X = Cl, Br) and subsequent hydrolysis.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Data availability

This compound is known and was identified by NMR (see above).

References

  1. Hill DG (2005) Boronic acids. Wiley-VCH

    Book  Google Scholar 

  2. Hill DG (2012) Boronic acids, 2nd edn. Wiley-VCH

    Google Scholar 

  3. Molander GA, Cavalcanti LN, Canturk B, Pan P-S, Kennedy LE (2009) J Org Chem 74:7364

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Kabalka GW, Coltuclu V (2009) Tetrahedron Lett 50:6271

    Article  CAS  Google Scholar 

  5. Blevins DW, Yao M-L, Yong L, Kabalka GW (2011) Tetrahedron Lett 52:6534

    Article  CAS  Google Scholar 

  6. Yuen AKL, Hutton CA (2005) Tetrahedron Lett 46:7899

    Article  CAS  Google Scholar 

  7. Lennox AJJ, Lloyd-Jones GC (2012) J Am Chem Soc 134:7431

    Article  CAS  PubMed  Google Scholar 

  8. Darses S, Genet JP (2008) Chem Revs 108:288

    Article  CAS  Google Scholar 

  9. Traister KM, Molander GA (2015) Topics Organomet Chem 49:117

    CAS  Google Scholar 

  10. Stefani HA, Cella R, Vieira AS (2007) Tetrahedron 63:3623

    Article  CAS  Google Scholar 

  11. Politanskaya LV, Selivanova GA, Panteleeva EV, Tretyakov EV, Platonov VE, Nikul’shin PV, Vinogradov AS, Zonov YaV, Karpov VM, Mezhenkova TV, Vasilyev AV, Koldobskii AB, Shilova OS, Morozova SM, Burgart YaV, Shchegolkov EV, Saloutin VI, Sokolov VB, Aksinenko AYu, Nenajdenko VG, Moskalik MYu, Astakhova VV, Shainyan BA, Tabolin AA, Ioffe SL, Muzalevskiy VM, Balenkova ES, Shastin AV, Tyutyunov AA, Boiko VE, Igumnov SM, Dilman AD, Adonin NYu, Bardin VV, Masoud SM, Vorobyeva DV, Osipov SN, Nosova EV, Lipunova GN, Charushin VN, Prima DO, Makarov AG, Zibarev AV, Trofimov BA, Sobenina LN, Belyaeva KV, Sosnovskikh VYa, Obydennov DL, Usachev SA (2019) Russ Chem Rev 88:425

    Article  CAS  Google Scholar 

  12. Ting R, Harwig CW, Lo J, Li Y, Adam MJ, Ruth TJ, Perrin DM (2008) J Org Chem 73:4662

    Article  CAS  PubMed  Google Scholar 

  13. Abo-Amer A, Frohn H-J, Steinberg C, Westphal U (2006) J Fluorine Chem 127:1311

    Article  CAS  Google Scholar 

  14. Frohn H-J, Adonin NYu, Bardin VV, Starichenko VF (2002) Z Anorg Allg Chem 628:2834

    Article  CAS  Google Scholar 

  15. Abo-Amer A, Adonin NYu, Bardin VV, Fritzen P, Frohn H-J, Steinberg C (2004) J Fluorine Chem 125:1771

    Article  CAS  Google Scholar 

  16. Frohn H-J, Franke H, Fritzen P, Bardin VV (2000) J Organomet Chem 598:127

    Article  CAS  Google Scholar 

  17. Adonin NYu, Babushkin DE, Parmon VN, Bardin VV, Kostin GA, Mashukov VI, Frohn H-J (2008) Tetrahedron 64:5920

    Article  CAS  Google Scholar 

  18. Shabalin AYu, Adonin NYu, Bardin VV, Taran OP, Ayusheev AB, Parmon VN (2013) J Fluorine Chem 156:290

    Article  CAS  Google Scholar 

  19. Shabalin AYu, Adonin NYu, Bardin VV, Prikhod’ko SA, Timofeeva MN, Bykova MV, Parmon VN (2013) J Fluorine Chem 149:82

    Article  CAS  Google Scholar 

  20. Shabalin AYu, Adonin NYu, Bardin VV (2017) Beilstein J Org Chem 13:703

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Adonin NYu, Bardin VV, Frohn H-J (2008) Collect Czech Chem Commun 73:1681

    Article  CAS  Google Scholar 

  22. Frohn H-J, Adonin NY, Bardin VV, Starichenko VF (2002) Z Anorg Allg Chem 628:2827

    Article  CAS  Google Scholar 

  23. El Dine TM, Rouden J, Blanchet J (2015) Chem Commun 51:16084

    Article  Google Scholar 

  24. Nöth H, Wrackmeyer B (1978) Nuclear Magnetic Resonance Spectroscopy of Boron Compounds. Springer, Berlin

    Book  Google Scholar 

  25. Zhang P, Kriegel RM, Frost JF (2016) ACS Sust Chem Eng 4:6991

    Article  CAS  Google Scholar 

  26. Bardin VV, Adonin NYu (2019) Monats Chem 150:1523

    Article  CAS  Google Scholar 

  27. Huchenski BSN, Christopherson CJ, Robertson KN, Speed AWH (2019) Org Biomol Chem 17:6158

    Article  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the MSHE RF (projects FWUR-2022-0002, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry and FWUR-2024-0035, G.K. Boreskov Institute of Catalysis). Authors would like to acknowledge the Multi-Access Chemical Research Center SB RAS for spectral and analytical measurements.

Funding

Ministry of science and high education,FWUR-2022-0002,Vadim V Bardin,FWUR-2024-0035,Nicolay Yu. Adonin

Author information

Authors and Affiliations

  1. N.N. Vorozhtsov, Novosibirsk Institute of Organic Chemistry, SB RAS, Acad. Lavrentiev Ave., 9, 630090, Novosibirsk, Russia

    Vadim V. Bardin

  2. G.K. Boreskov Institute of Catalysis, SB RAS, Acad. Lavrentiev Ave., 5, 630090, Novosibirsk, Russia

    Nicolay Yu. Adonin

Authors
  1. Vadim V. Bardin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nicolay Yu. Adonin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vadim V. Bardin.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bardin, V.V., Adonin, N.Y. Preparation of arylboronic and diarylborinic acids from potassium aryl(fluoro)borates. Monatsh Chem (2024). https://doi.org/10.1007/s00706-024-03213-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00706-024-03213-4

Keywords

Search

Navigation