The synthesis of γ-benzo[b]furanyl malonates was achieved through the addition of benzo[b]furan to activated cyclopropanes. These Friedel-Crafts reactions were catalyzed by calcium bis(trifluoromethanesulfonimide), Ca(NTf2)2 with tetrabutylammonium hexafluorophosphine as a co-catalyst. The additions proceeded with complete regioselectivity and in good to excellent yield. Optimization of the reaction conditions and investigation into the scope of the methodology with regards to substitution on the cyclopropane are reported.