Premium
A Universal Procedure for the [ 18 F]Trifluoromethylation of Aryl Iodides and Aryl Boronic Acids with Highly Improved Specific Activity
Author(s) -
van der Born Dion,
Sewing Claudia,
Herscheid J. Koos D. M.,
Windhorst Albert D.,
Orru Romano V. A.,
Vugts Danielle J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201406221
Subject(s) - trifluoromethylation , aryl , chemistry , iodide , boronic acid , combinatorial chemistry , organic chemistry , trifluoromethyl , alkyl
Herein, we describe a valuable method for the introduction of the [ 18 F]CF 3 group into arenes with highly improved specific activity by the reaction of [ 18 F]trifluoromethane with aryl iodides or aryl boronic acids. This [ 18 F]trifluoromethylation reaction is the first to be described in which the [ 18 F]CF 3 products are generated in actual trace amounts and can therefore effectively be used as PET tracers. The method shows broad scope with respect to possible aryl iodide and aryl boronic acid substrates, as well as good to excellent conversion. In particular, the [ 18 F]trifluoromethylation of boronic acids was found to outperform [ 18 F]trifluoromethylation reactions of halogenated aryl precursors with regard to conversion, reaction conditions, and kinetics.