Fluoro-decarboxylation of pyrrolecarboxylic acids by F–TEDA–BF4– a convenient general synthesis of fluoropyrroles

Abstract

Reaction of a range of α-pyrrolecarboxylic acids, in which the ring is highly substituted by electron-withdrawing or -donating groups, with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis (tetrafluoroborate)(F–TEDA–BF₄) gives the corresponding α-fluoropyrroles in 32–47% yields; 2-fluoroporphobilinogen (F–PBG), of potential use as an inhibitor of the enzyme porphobilinogen (PBG) deaminase, has been synthesized by this method.