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Org Lett. 2016 May 6;18(9):2020-3. doi: 10.1021/acs.orglett.6b00629. Epub 2016 Apr 27.

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

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Precursory Research for Embryonic Science and Technology, Japan Science and Technology Agency , 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.


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.

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