Electrochemical Dearomative Halocyclization of Tryptamine and Tryptophol Derivatives
Kun Liu, Yuqi Deng, Wenxu Song, Chunlan Song, Aiwen Lei
Abstract
Summary of main observation and conclusion 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.
Topics & Concepts
ChemistryTryptamineElectrolysisElectrochemistryHalideCombinatorial chemistryElectrolyteOrganic chemistryBiochemistryElectrodePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions