A new protocol is herein described for the direct generation of alkylated indolo/benzoimidazo[2,1-a]isoquinolin-6(5H)-one derivatives by using Hantzsch esters as alkylation radical precursors using a photoredox/K₂S₂O₈ system. This oxidative alkylation of active alkenes involves a radical cascade cyclization process and a sequence of Hantzsch ester single electron oxidation, C–C bond cleavage, alkylation, arylation and oxidative deprotonation.