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Transition-metal-catalyzed cross-coupling reactions as very efficient and atom-economical approaches have been widely used to build up complex heterocyclic compounds. However, modification of 2-oxyl benzimidazole skeleton using maleimide compounds via C–H activation has remained unprecedented. Herein, we developed a rhodium(III)-catalyzed [5 ​+ ​1] cascade spiroannulation to construct diversified novel benzimidazole-incorporated spirosuccinimide derivatives from 2-oxyl benzimidazoles and maleimides.