Free radical carbochloromethylations of ortho-cyanoarylacrylamides and N-(arylsulfonyl)acrylamides have been developed by employing simple alkyl chlorides as the chloromethyl source. The transformations are characterized by wide functional group compatibility and utilizing readily available reagents, thus providing efficient methods for constructing polychloromethyl-substituted quinoline-2,4-diones and α-aryl-β-polychloromethylated amides.