An　efficient　method　for　the　copper-catalyzed　selective　CH　difluoroalkylation　of　coumarins　and　with　low　cost　and　readily　available　ethyl　bromodifluoroacetate　and　N-phenyl　bromodifluoroacetamide　has　been　reported.　This　reaction　exhibits　good　functional　group　tolerance　with　respect　to　coumarins　and　difluoroalkylation　reagents,　and　several　redox-sensitive　substrates　have　been　successfully　CH　difluoroalkylated　in　good　to　high　yield.　This　design　could　further　expand　the　scope　to　other　heteroarenes,　including　furan,　benzofuran,　pyrrole,　pyridinone,　chromenone,　indole,　and　quinolinone.　A　mechanism　involving　copper-catalyzed　in-situ　generation　of　fluoroalkyl　radical　is　proposed.　©　2020　Wiley-VCH　GmbH