2-Fluoroindoles　are　an　important　structural　scaffold　in　many　bioactive　or　therapeutic　agents,　but　efficient　constructions　of　2-fluoroindole　derivatives　are　very　sparce.　Here　the　authors　report　an　efficient　and　general　strategy　for　the　construction　of　2-fluoroindoles　in　which　a　wide　variety　of　2-fluoroindoles　were　accessed　with　high　efficiency　and　chemoselectivity.　2-Fluoroindoles　as　an　important　structural　scaffold　are　widely　existing　in　many　bioactive　or　therapeutic　agents.　Despite　their　potential　usefulness,　efficient　constructions　of　2-fluoroindole　derivatives　are　very　sparce.　The　development　of　straightforward　synthetic　approaches　to　access　2-fluoroindoles　is　highly　desirable　for　studying　their　fundamental　properties　and　applications.　Herein,　we　report　an　efficient　and　general　strategy　for　the　construction　of　2-fluoroindoles　in　which　a　wide　variety　of　2-fluoroindoles　were　accessed　with　high　efficiency　and　chemoselectivity.　Instead　of　starting　from　indole　skeletons,　our　strategy　constructs　indole　scaffolds　alongside　the　incorporation　of　fluorine　atom　on　C2　position　in　a　formal　[4+1]　cyclization　from　readily　accessible　ortho-vinylanilines　and　difluorocarbene.　In　our　protocol,　commercially　accessible　halodifluoroalkylative　reagents　provide　one　carbon　and　one　fluorine　atom　by　cleaving　one　C-N　tertiary　bond　and　forming　one　C-N　bond　and　one　C-C　double　bond　with　ortho-vinylanilines.　Downstream　transformations　on　2-fluoroindoles　lead　to　various　valuable　bioactive　molecules　which　demonstrated　significant　synthetic　advantages　over　previous　reports.　And　mechanistic　studies　suggest　that　the　reaction　undergoes　a　cascade　difluorocarbene-trapping　and　intramolecular　Michael　addition　reaction　followed　by　Csp(3)-F　bond　cleavage.