Hybrid Lewis acid/hydrogen-bond donor receptor for fluoride.

abstract

• [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.

authors

• Gabbai, Francois

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

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• Infectious Diseases

PubMed Central ID

• 16774247

Digital Object Identifier (DOI)

• 10.1021/ol060791v

start page

• 2747

end page

• 2749

volume

• 8

issue

• 13

URL

• http://dx.doi.org/10.1021/ol060791v