posted on 2023-12-13, 16:35authored byJie Huang, Jin-Quan Li, Xin-Yue Cui, Yi-Han Qin, Shi-Jie Ma, Zi-An An, Wen-Wu Sun, Bin Wu
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.