A radical cascade cyclization of 2-alkynylaniline derivatives with sulfonyl chlorides was developed to construct C3sulfone methylene-substituted indolines in yields of 21 to 85% with a broad substrate scope under metal-and base-free conditions. This protocol could simultaneously build three new chemical bonds and employ a solvent-radical relay strategy, providing a rapid and concise approach toward an indoline framework. Scale-up reactions of this method and further transformations to afford useful indolines were also demonstrated.