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Both the pyrroloindoline core and N-CF 3 moiety hold significant importance in medicinal chemistry. However, to date, no instances of constructing N-CF 3 -containing pyrroloindolines have been reported. Herein, we present a robust and operationally simple approach to assembling such intriguing skeletons from tryptamine-derived isocyanides through a cascade sequence, which includes an oxidative trifluorination and a subsequent halogenative cyclization. Key to the success lies in the development of a facile conversion of isocyanides to N-CF 3 moiety with commercially available reagents N-halosuccinimide and Et 3 N·HF. The protocol features mild reaction conditions, broad functional group tolerance, good to excellent yields, and high diastereoselectivities. In addition, we demonstrate that the halide substituent within the products serves as a versatile functional handle for accessing diverse C3-quaternary-substituted N-CF 3 -pyrroloindolines., (© 2024. The Author(s).)