A silver-catalyzed formal [3 + 2] cycloaddition reaction, with cyclopropanols as a C3 subunit and imines as a two-atom subunit, is developed. The reaction takes place under mild conditions and produces a broad array of polysubstituted pyrroles in medium to high yields. It represents the first example of oxidative radical addition to imines, thus offering a new choice for the direct C-H functionalization of imines.