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Regioselective Electrophilic Trifluoromethylation of Indolines, Oxindolines and Indoles in Superacid.

✍ Scribed by Sebastien Debarge; Kenza Kassou; Helene Carreyre; Bruno Violeau; Marie-Paule Jouannetaud; Jean-Claude Jacquesy


Book ID
111699555
Publisher
John Wiley and Sons
Year
2004
Weight
117 KB
Volume
35
Category
Article
ISSN
0931-7597

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Regioselective electrophilic trifluorome
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In a one pot procedure, treatment of chloro or methyl substituted acetanilides in HF/SbF 5 /CCl 4 followed by addition of HF/pyridine yields trifluoromethyl derivatives with high regioselectivity.

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In SbFS-HF, indolines and indoles are hydroxylated on the aromatic ring, protonated hydrogen peroxide H302+ reacting on the protonated substrates. Electrophilic hydroxylation of aromatics has been intensively studied and it has been shown that hydrogen peroxide in superacidic media is a convenient r