Reactivity of Indole as an Electrophile and Its Application for the Synthesis of 2-Phenylindole and 3-Phenylindole

Tajima, Nobumitsu; Nakatsuka, Shin‐ichi

doi:10.1515/hc.2000.6.1.59

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Cited by 4 publications

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“…The authors have cited additional references within the Supporting Information. [24][25][26][27][28][29]…”

Section: Supporting Informationmentioning

confidence: 99%

On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A

Tokushige,

Abe

2024

Chemistry A European J

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In this work, a straightforward synthesis of C3‐N1’ bisindolines is achieved by a formal umpolung strategy. The protocols were tolerant of a wide variety of substituents on the indole and indoline ring. In addition, the C3‐N1’ bisindolines could be converted to C3‐N1’ indole‐indolines and C3‐N1’‐bisindoles. Also, we have successfully synthesized (±)‐rivularin A through a biomimetic late‐stage tribromination as a key step.

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“…The authors have cited additional references within the Supporting Information. [24][25][26][27][28][29]…”

Section: Supporting Informationmentioning

confidence: 99%

On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A

Tokushige,

Abe

2024

Chemistry A European J

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“…For transformations at the C2 position of indoles, dehydrogenative silylation using an earth-abundant metal catalyst was recently reported . Generally, electrophilic addition reactions have been investigated via the formation of indolium intermediates to produce indoline derivatives . Unfortunately, the latent nucleophilicity of indole at the C3 position facilitates dimerization .…”

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confidence: 99%

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

Morimoto

Morioku

Suzuki³

et al. 2016

Org. Lett.

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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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Recent Advances in the Catalytic Functionalization of “Electrophilic” Indoles

Cerveri

Bandini

2020

Chin. J. Chem.

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Reactivity of Indole as an Electrophile and Its Application for the Synthesis of 2-Phenylindole and 3-Phenylindole

Cited by 4 publications

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On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A

On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A

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

Recent Advances in the Catalytic Functionalization of “Electrophilic” Indoles

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