An efficient method for the selective benzylic C-H alkylation of sulfonamides using maleimides has been developed. The reaction proceeds via the benzylic C(sp3)-H bond activation of sulfonamide in the presence of a Pd(II) catalyst without requiring any oxidant, additive, or external ligand. This methodology is highly compatible with a wide variety of substituted maleimides. A plausible reaction mechanism is also proposed to account for this alkylation reaction.