Hybrid Lewis acid/hydrogen-bond donor receptor for fluoride. Academic Article uri icon


  • [reaction: see text] To verify if hydrogen-bond donor groups can assist fluoride binding at the boron center of triaryl boranes, o-(dimesitylboryl)trifluoroacetanilide has been synthesized. Reaction of this new borane with [n-Bu(4)N][F] in acetone affords the corresponding fluoroborate complex whose stability constant exceeds that of [Mes(3)BF](-) by at least 2 orders of magnitude. Presumably, the higher fluoride affinity of o-(dimesitylboryl)trifluoroacetanilide results from the cooperativity of the Lewis acidic boron center and the hydrogen-bond donor trifluoroacetamide group.

published proceedings

  • Org Lett

author list (cited authors)

  • Hudnall, T. W., Melami, M., & Gabbai, F. P.

citation count

  • 94

complete list of authors

  • Hudnall, Todd W||Melaïmi, Mohand||Gabbaiï, François P

publication date

  • June 2006