A　divergent　strategy　for　precise　construction　of　SCF2H　or　SeCF2H　groups　on　heteroarenes　generated　in　situ　from　CF3-containing　1,3-enynes　was　developed.　Reactions　of　readily　available　1,3-enynes　with　S-8　and　ClCF2H　provided　3-SCF2H-4-CF3-thiophenes　via　a　cascade　thiophene　construction/selective　C3　position　thiolation/difluoromethylthiolation　process,　as　did　a　series　of　3-SeCF2H-4-CF3-selenophenes　by　similar　strategies.　The　plausible　radical　annulation　process　for　the　construction　of　the　thiophene　ring　and　difluorocarbene　generated　in　situ　was　confirmed　by　experiment.