Download PDF
Synthesis 2011(2): 292-302  
DOI: 10.1055/s-0030-1258370
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

HF-Free, Direct Synthesis of Tetrabutylammonium Trifluoroborates

G. K. Surya Prakash*, Fabrizio Pertusati, George A. Olah*
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661, USA
Fax: +1(213)7406679; e-Mail: gprakash@usc.edu;
Further Information

Publication History

Received 3 September 2010
Publication Date:
15 December 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The direct preparation of tetrabutylammonium trifluoroborates from boronic acids without using HF or the corresponding potassium salt is described. The method is highly efficient for aromatic and aliphatic boronic acids. This protocol, however, was less efficient for boronic acids that were sensitive to protiodeboronation.

Key words

trifluoroborates - tetrabutylammonium bifluoride - synthesis - HF-free - boronic acid

    References

  • 1 Vedejs E. Chapman RW. Fields SC. Lin S. Schrimpf MR. J. Org. Chem.  1995,  60:  3020 
    CrossrefGoogle Scholar
  • 2 Darses S. Genêt J.-P. Brayer J.-L. Demoute J.-P. Tetrahedron Lett.  1997,  38:  4393 
    CrossrefGoogle Scholar
  • 3 Puentener K, and Scalone M. inventors; EP Patent 1057831  A2. 
  • For selected examples, see:
  • 4a Molander GA. Ribagorda M. J. Am. Chem. Soc.  2003,  125:  11148 
    Google Scholar
  • 4b Molander GA. Figueroa R. J. Org. Chem.  2006,  71:  6135 
    Google Scholar
  • 4c Molander GA. Petrillo DE. J. Am. Chem. Soc.  2006,  128:  9634 
    Google Scholar
  • 4d Molander GA. Jean-Gerard L. J. Org. Chem.  2007,  72:  8422 
    Google Scholar
  • 4e Molander GA. Sandrock DL. Org. Lett.  2007,  9:  1597 
    Google Scholar
  • 5a Darses S. Genêt JP. Eur. J. Org. Chem.  2003,  4313 
    Google Scholar
  • 5b Molander GA. Figueroa R. Aldrichimica Acta  2005,  38:  49 
    Google Scholar
  • 5c Molander GA. Ellis N. Acc. Chem. Res.  2007,  40:  275 
    Google Scholar
  • 5d Stefani HA. Cella R. Adriano S. Tetrahedron  2007,  63:  3623 
    Google Scholar
  • 5e Darses S. Genêt J.-P. Chem. Rev.  2008,  108:  288 
    Google Scholar
  • 6a Darses S. Michaud G. Genet J.-P. Eur. J. Org. Chem.  1999,  1875 
    Google Scholar
  • 6b Molander GA. Ito TI. Org. Lett.  2001,  3:  393 
    Google Scholar
  • 6c Molander GA. Yun CS. Ribagorda M. Biolatto B. J. Org. Chem.  2003,  68:  5534 
    Google Scholar
  • 7 Murphy JM. Tzschucke CC. Hartwig JF. Org. Lett.  2007,  9:  757 
    CrossrefPubMedGoogle Scholar
  • 8 Vedejs E. Fields SC. Hayashi R. Hitchcock SR. Powell DR. Schrimpf MR. J. Am. Chem. Soc.  1999,  121:  2460 
    CrossrefGoogle Scholar
  • 9 Batey RA. Quach TD. Tetrahedron Lett.  2001,  42:  9099 
    CrossrefGoogle Scholar
  • 10a Bosch P. Camps F. Chamorro E. Gasol V. Guerrero A. Tetrahedron Lett.  1987,  28:  4733 
    Google Scholar
  • 10b Camps F. Chamorro E. Gasol V. Guerrero A. J. Org. Chem.  1989,  54:  4294 
    Google Scholar
  • 10c Chakraborty D. Horchler S. Roesky HW. Noltemeyer M. Schmidt H.-G. Inorg. Chem.  2000,  39:  3995 
    Google Scholar
  • 10d Huang A. Li H.-Q. Massefski W. Saiah E. Synlett  2009,  2518 
    Google Scholar
  • 10e Kim K.-Y. Kim BC. Lee HB. Shin H. J. Org. Chem.  2008,  73:  8106 
    Google Scholar
  • 10f Landini D. Penso M. Tetrahedron Lett.  1990,  31:  7209 
    Google Scholar
  • 11a Adonin NY. Bardin VV. Floerke U. Frohn H.-J. Z. Anorg. Allg. Chem.  2005,  631:  2638 
    Google Scholar
  • 11b Adonin NY. Bardin VV. Frohn H.-J. Collect. Czech. Chem. Commun.  2008,  73:  1681 
    Google Scholar
  • 11c Adonin NY. Bardin VV. Frohn H.-J. Main Group Met. Chem.  2009,  32:  109 
    Google Scholar
  • 12 Landini D. Molinari H. Penso M. Rampoldi A. Synthesis  1988,  953 
    Article in Thieme ConnectGoogle Scholar
  • 13a Molander GA. Cooper DJ. J. Org. Chem.  2007,  72:  3558 
    Google Scholar
  • 13b Molander GA. Petrillo DE. J. Am. Chem. Soc.  2006,  128:  9634 
    Google Scholar
  • 14 Wallace DJ. Chen CYi. Tetrahedron Lett.  2002,  43:  6987 
    CrossrefGoogle Scholar
  • 15a Molander GA. Canturk B. Kennedy LE. J. Org. Chem.  2009,  74:  973 
    Google Scholar
  • 15b Tyrrell E. Brookes P. Synthesis  2003,  469 
    Google Scholar
  • 15c Boronic Acids   Hall DG. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 16a Mesmer RE. Rutenbeerg AC. Inorg. Chem.  1973,  12:  699 
    Google Scholar
  • 16b Fox MA. Gill WR. Herbertson PL. MacBride JAH. Wade K. Colquhoun HM. Polyhedron  1996,  15:  565 
    Google Scholar
  • 16c Fox MA. MacBride JAH. Wade K. Polyhedron  1997,  16:  2499 
    Google Scholar
  • See for example:
  • 17a Kuivila HG. Nahabedian KV.
    J. Am. Chem. Soc.  1961,  83:  2159 
    Google Scholar
  • 17b Nahabedian KV. Kuivila HG. J. Am. Chem. Soc.  1961,  83:  2167 
    Google Scholar
  • 17c Kuivila HG. Reuwer JF. Mangravite JA. J. Am. Chem. Soc.  1964,  86:  2666 
    Google Scholar
  • 17d Brown RD. Buchanan AS. Humffray AA. Aust. J. Chem.  1965,  18:  1521 
    Google Scholar
  • 17e Fuller AA. Hester HR. Salo EV. Stevens EP. Tetrahedron Lett.  2003,  44:  2935 
    Google Scholar
  • 17f Klingensmith LM. Bio MM. Moniz GA. Tetrahedron Lett.  2007,  48:  8242 
    Google Scholar
  • 18 Restorp P. Berryman OB. Sather AC. Ajami D. Rebek J. Chem. Commun.  2009,  5692 
    Google Scholar