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

Naoki Morimoto; Kumika Morioku; Hideyuki Suzuki; Yasuo Takeuchi; Yuta Nishina

doi:10.1021/acs.orglett.6b00629

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

Naoki Morimoto, Kumika Morioku, Hideyuki Suzuki, Yasuo Takeuchi, Yuta Nishina

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	2020-2023
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.6b00629
Publication status	Published - May 6 2016

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00629

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abstract = "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.",

author = "Naoki Morimoto and Kumika Morioku and Hideyuki Suzuki and Yasuo Takeuchi and Yuta Nishina",

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T1 - Lewis Acid and Fluoroalcohol Mediated Nucleophilic Addition to the C2 Position of Indoles

AU - Morimoto, Naoki

AU - Morioku, Kumika

AU - Suzuki, Hideyuki

AU - Takeuchi, Yasuo

AU - Nishina, Yuta

PY - 2016/5/6

Y1 - 2016/5/6

N2 - 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.

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

Abstract

ASJC Scopus subject areas

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