An　efficient　and　regioselective　synthesis　of　highly　substituted　2-trifluoromethyl　pyrrole　derivatives　via　silver-catalyzed　cyclization　of　vinyl　azides　with　ethyl　4,4,4-trifluoro-3-oxobutanoate　is　reported.　Various　alpha-(heteo)aryl,　alkyl,　alpha-aryl,　as　well　as　alpha,beta-disubstituted　vinyl　azides,　participate　in　this　transformation.　The　reaction　mechanism　likely　involves　the　addition　of　in　situ　generated　2H-azirine　to　the　diketone　species,　followed　by　intramolecular　addition,　N-C-1　cleavage,　and　elimination.