AbstractA practical method for the synthesis of hydroxyalkylated indolo[2,1-a]isoquinoline derivatives through the metal-free cascade cyclization of 2-arylindoles with alcohols in the presence of tert-butyl hydroperoxide (TBHP) is disclosed. The present method features transition-metal-free conditions and exceptional functional group tolerance. A series of valuable hydroxyalkylated indolo[2,1-a]isoquinoline derivatives bearing various functional groups is synthesized in moderate to excellent yields.