Herein we report an efficient two-carbon homologated variant of Friedel-Crafts alkylation via photochemical radical alkene stitching. Readily available feedstock alkenes are used as bridges between photogenerated alkyl radicals and arenes, opening a route to γ-aryl-carbonyls for chemo-divergent access to aryltetralone and γ-lactones, a gateway to 2,7'-cyclolignans.