Abstract Click to copy section linkSection link copied! Despite their inherently high nucleophilicity, pyrroles have rarely been explored in Friedel–Crafts-type alkylation reactions with donor–acceptor cyclopropanes (DACs). Herein, we report the first examples of such reactions of 1,2,5-trisubstituted pyrroles using DACs. Catalyzed by Sc(OTf)3, the reaction provides efficient access to 1,2,3,5-tetrasubstituted pyrroles─an important class of bioactive compounds─in yields up to 93%.