Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 8, pp 1523–1531 | Cite as

The preparation of pentafluorophenyldihaloboranes from pentafluorophenylmercurials C6F5HgR and BX3: the dramatic dependence of the reaction direction on the ligand R

  • Vadim V. BardinEmail author
  • Nicolay Yu. Adonin
Original Paper


In search of convenient preparations of C6F5BX2 (X = Cl, Br), reactions of C6F5HgR (R = C6F5, C6H5, C2H5, Br and Cl) with BX3 were studied. Under the action of BCl3 the order of the C–Hg bond cleavage is C6F5Hg–C6H5 > C6F5–HgC2H5 > C6F5–HgC6F5  >> C6F5–HgCl. With more reactive BBr3 the sequence is C6F5Hg–C6H5 > C6F5–HgC2H5 ~ C6F5Hg–C2H5 > C6F5–HgC6F5 ≥ C6F5–HgBr. During the study we found the simple way to alkyldibromoboranes which is presented by the preparation of C2H5BBr2 from C2H5HgBr and BBr3. It is the second example of synthesis of alkylmercury derivative in an addition to the earlier reported formation of cyclopropylmercurials from di(cyclopropyl)mercury and BX3.

Graphic abstract


Main group compounds NMR spectroscopy Transmetallation Organometallic compounds 



The work was supported by Ministry of Science and Higher Education of the Russian Federation. Authors also would like to acknowledge the Multi-Access Chemical Research Center SB RAS (Novosibirsk) for spectral and analytical measurements.


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic ChemistrySB RASNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia
  3. 3.G. K. Boreskov Institute of CatalysisSB RASNovosibirskRussia

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