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Updated: Jul 8, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
A Method for the Synthesis of Thioindoles through Copper-Catalyzed C-S Bond Coupling Reaction
Jie Huang1, Jin-Quan Li2, Xin-Yue Cui2
1School of Pharmaceutical Sciences & School of Chemistry and Materials Science, South-Central Minzu University, Wuhan 430074, China.
Abstract:
We herein report the copper-catalyzed C-S bond coupling reaction of indoles with N-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.
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