A base-promoted cascade radical difluoroalkylation/cyclization of acrylamides with ICF2COOEt to synthesize CF2-containing oxindoles and isoquinoline-1,3-diones in moderate to excellent yields was developed under transition metal-free and catalyst-free conditions. This reaction tolerated a variety of functional groups and provided an alternative and mild method for the preparation of difluoroester-substituted fiveand six-membered nitrogen-containing heterocyclic products.