An unprecedented benzylic C-H functionalization of methyl arenes across unactivated alkenes is presented. In the presence of MnCl2·4H2O and di- tert-butyl peroxide, N-allyl anilines underwent benzylation/cyclization cascade to give benzylated indolines, which are a previously unmet synthetic goal. This protocol features simple operation, broad substrate scope, and great exo selectivity.