Synthetic methods for unsymmetrical aminodisulfides are greatly needed due to their applications in drug discovery, linker chemistry, and materials sciences. In this study, an amination reaction of N-dithiophthalimides has been developed for the divergent synthesis of unsymmetrical aminodisulfides. The reaction proceeds under mild conditions and provides the aminodisulfides in excellent yields without cleavage of the disulfide bond. The N-dithiophthalimides are readily available from several bilateral disulfurating reagents, and the broad substrate scope of this reaction allows for the modular synthesis of a variety of unsymmetrical aminodisulfides in two-step operations.