Silver-Catalyzed Domino Reaction of CF 3 -Substituted N -Allenamides with Primary Amines for the Construction of 2-Amido-5-fluoropyrroles.

We report herein a domino reaction to construct 2-amido-5-fluoropyrroles from CF 3 -substituted N -allenamides. The in situ generated gem -difluorinated ene-ynamides derived from CF 3 -substituted N -allenamides, when subjected to silver catalysis with a primary amine, undergo simultaneous hydroamination of the ynamide moiety followed by a 5- endo-trig addition/β-fluoride elimination sequence, enabling the construction of 2-amido-5-fluoropyrroles. This transformation features excellent functional group compatibility. By employing 2-aminophenols, functionalized benzo-oxazoles were produced.