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[3 + 2] Cycloaddition reactions of heteroaromatic <i>N</i>-ylides with electron-deficient olefins have been developed. The heteroaromatic <i>N</i>-ylides, in situ generated from <i>N</i>-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-<i>c</i>]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also carried out to verify the practicability of the methodology.