Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 si...

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Veröffentlicht in:Organic letters 2016-05, Vol.18 (9), p.2020-2023
Hauptverfasser: Morimoto, Naoki, Morioku, Kumika, Suzuki, Hideyuki, Takeuchi, Yasuo, Nishina, Yuta
Format: Artikel
Sprache:eng
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Zusammenfassung:Indole readily undergoes nucleophilic substitution at the C3 site, and many indole derivatives have been functionalized using this property. Indole also forms indolium, which allows electrophilic addition in acidic conditions, but current examples have been limited to intramolecular reactions. C2 site-selective nucleophilic addition to indole derivatives using fluoroalcohol and a Lewis acid was developed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00629