One-step syntheses of carbocycles substituted with amines from simple starting materials remain rare. We recently developed an intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enables this one-step synthesis. Herein, we report our findings for a full-scale study of the annulation. Significant expansion of the substrate scope for both cyclopropylanilines and alkynes has been achieved. A range of structurally diverse carbocycles substituted with amines is prepared.