An　electrochemical　intramolecular　5-exo-dig　aza-cyclization　of　2-alkynylbenzamides　and　subsequent　nucleophilic　fluorination　have　been　developed　to　afford　the　highly　selective　synthesis　of　mono-　and　trifluorinated　isoindolin-1-one　derivatives.　This　work　demonstrates　the　unique　capability　of　synthetic　electrochemistry　in　controlling　reaction　selectivity　through　the　applied　electrolytic　parameters.　In　addition,　the　obtained　monofluorinated　3-methyleneisoindolin-1-one　(19)　displays　interesting　photophysical　properties　that　are　not　observed　in　its　nonfluorinated　analog.