Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 1, Pages 161-172Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201701074
Keywords
Indole; Umpolung; Hydroarylation; BrOnsted acid; Friedel-Crafts
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Funding
- People Programme (Marie Curie Actions) of the European Union's Seventh Framework Programme FP7 under REA grant [623422]
- MENESR
- ANR [ANR-12-JS07-0002]
- Universite Paris Sud
- CNRS
- Agence Nationale de la Recherche (ANR) [ANR-12-JS07-0002] Funding Source: Agence Nationale de la Recherche (ANR)
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We report that triflic acid, a strong BrOnsted acid, is a very powerful alternative to FeCl3 to mediate the hydroarylation of N-Ac indoles, which delivers regioselectively 3-arylindolines, 3,3-spiroindolines or 2-arylindolines. Mechanistic explorations point towards the existence of a highly electrophilic intermediate by simultaneous activation of the acetyl and of the C2=C3 bond by protons.
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