Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides

Alexander J. Cresswell, Stephen G. Davies, Aude L. A. Figuccia, Ai M. Fletcher, Dorus Heijnen, James A. Lee, Melloney J. Morris, Alice M. R. Kennett, Paul M. Roberts, James E. Thomson

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7 Citations (Scopus)

Abstract

The incorporation of alkoxy ligands within a range of alkoxyfluoroboranes and dialkoxyfluoroboranes results in fluoroborane reagents with attenuated Lewis acidity and increased ability to donate fluoride ion(s) when compared to boron trifluoride itself. Pinacolatoboron fluoride (pinBF), prepared in situ from BF3·OEt2 and bis(O-trimethylsilyl)pinacol, has been identified as an efficient fluoride donor which allows highly stereoselective SN1-type epoxide ring-opening (with retention of configuration) of a range of trans-β-methyl-substituted aryl epoxides to give the corresponding syn-fluorohydrins. The substrate scope of this transformation is more broad than the analogous protocol using boron trifluoride alone.

Original languageEnglish
Pages (from-to)3373-3377
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
Publication statusPublished - 3 Jun 2015

Keywords

  • Benzylic fluoride
  • Epoxide
  • Nucleophilic fluorination

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Cresswell, A. J., Davies, S. G., Figuccia, A. L. A., Fletcher, A. M., Heijnen, D., Lee, J. A., Morris, M. J., Kennett, A. M. R., Roberts, P. M., & Thomson, J. E. (2015). Pinacolatoboron fluoride (pinBF) is an efficient fluoride transfer agent for diastereoselective synthesis of benzylic fluorides. Tetrahedron Letters, 56(23), 3373-3377. https://doi.org/10.1016/j.tetlet.2014.12.044