A Method for the Synthesis of Thioindoles through Copper-Catalyzed C–S Bond Coupling Reaction
Jie Huang, Jinquan Li, Xinyue Cui, Yi-Han Qin, Shi-Jie Ma, Zi-An An, Wen‐Wu Sun, Bin Wu
Abstract
-thiosuccinimides, resulting in moderate to excellent yields of mono- and bis-sulfenylated compounds such as arylthioindoles, alkylthioindoles, selenylated indoles, and cysteine-substituted indoles. Thioarylation and thioglycosylation at the C2 position of indole alkaloids in the Radix Isatidis were achieved via structural modification. The first total syntheses of isatindigotindolosides III and IV have been successfully carried out. The electrophilic sulfenyl bromides generated in situ can play an important role in the catalytic cycle.
Topics & Concepts
Indole testCatalysisChemistryElectrophileCopperCoupling reactionCombinatorial chemistryMedicinal chemistryCoupling (piping)StereochemistryOrganic chemistryMaterials scienceMetallurgySulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions