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Silver-catalyzed Vinylic C–F Bond Activation: Synthesis of 2-Fluoroindoles from β,β-Difluoro-o-sulfonamidostyrenes
Author(s) -
Takeshi Fujita,
Yota Watabe,
Shigeyuki Yamashita,
Hiroyuki Tanabe,
Tomoya Nojima,
Junji Ichikawa
Publication year - 2016
Publication title -
chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.492
H-Index - 114
eISSN - 1348-0715
pISSN - 0366-7022
DOI - 10.1246/cl.160427
Subject(s) - chemistry , catalysis , medicinal chemistry , stereochemistry , polymer chemistry , organic chemistry
An electrophilic 5-endo-trig cyclization of β,β-difluoro-o-sulfonamidostyrenes was performed in 1,1,1,3,3,3-hexafluoropropan-2-ol using a Ag(I) catalyst and N,O-bis(trimethylsilyl)acetamide. In this process, vinylic C–F bond activation was achieved via silver-catalyzed β-fluorine elimination, accompanied by C–N bond formation, which led to the synthesis of 2-fluoroindoles.

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