Nucleophilic fluorination reactions starting from aqueous fluoride ion solutions.

abstract

• 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.

authors

• Gabbai, Francois

published proceedings

• Org Lett

author list (cited authors)

• Zhao, H., & Gabbai, F. P.

citation count

• 53

complete list of authors

• Zhao, Haiyan||Gabbaiï, François P

publication date

• March 2011

publisher

• American Chemical Society (ACS)  Publisher

published in

• Organic Letters  Journal

keywords

• 0306 Physical Chemistry (incl. Structural)

PubMed Central ID

• 21332154

Digital Object Identifier (DOI)

• 10.1021/ol200129q

start page

• 1444

end page

• 1446

volume

• 13

issue

• 6

URL

• http://dx.doi.org/10.1021/ol200129q