Abstract: | Owing to the easy functionalization of 3‐haloindolines to many biologically active compounds, extensive efforts have been made for their efficient preparation. Herein, an electrochemical dearomative bromo‐ and chloro‐cyclization of tryptamine and tryptophol derivatives has been developed under undivided electrolytic conditions. In this protocol, neither external chemical oxidants nor harsh conditions are needed, and a wide range of substituted hexahydropyrroloindolines/tetrahydrofuroindolines are obtained with halide ion in high efficiencies. Moreover, this electrolysis could also be scaled up to gram synthesis with good yields. |