Nucleophilic fluorination reactions starting from aqueous fluoride ion solutions. Academic Article uri icon


  • The sulfonium borane 2(+) reacts with fluoride anions in MeOH/H(2)O mixtures to afford the zwitterionic fluoroborate 2-F as an easily isolable nonhygroscopic solid. In dry acetonitrile, 2-F reacts with PhS(-) to afford the anionic fluoroborate 1-F(-). The latter is very labile and acts as a nucleophilic fluorination reagent toward a variety of substrates including alkylhalides and electron-deficient aromatic compounds. This approach may become broadly applicable to nucleophilic fluorination procedures that involve wet fluoride sources.

published proceedings

  • Org Lett

author list (cited authors)

  • Zhao, H., & Gabbai, F. P.

citation count

  • 51

complete list of authors

  • Zhao, Haiyan||Gabbaiï, François P

publication date

  • March 2011