Potassium <i>tert</i>‐Butoxide‐Mediated Ring‐Opening of Indolines: Concise Synthesis of 2‐Vinylanilines

Abstract A concise and metal‐free procedure has been developed for the synthesis of 2‐vinylanilines. Reactions of indolines with tert ‐BuOK in DMSO afford the decorated 2‐vinylanilines in yields up to 92 %. In addition, the 2, or 3‐substituted indolines could be converted to trisubstituted alkenes. Also, the protocol can be scaled to afford gram quantities of the decorated 2‐vinylanilines.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-11-25
DOI
https://doi.org/10.1002/ajoc.202400552
Primary Topic
Chemical Synthesis and Analysis
Type
article
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article

Potassium tert‐Butoxide‐Mediated Ring‐Opening of Indolines: Concise Synthesis of 2‐Vinylanilines

Keisuke Tokushige, Takumi Abe, Shota Asai
Asian Journal of Organic Chemistry
Chemical Synthesis and Analysis
article

Potassium tert‐Butoxide‐Mediated Ring‐Opening of Indolines: Concise Synthesis of 2‐Vinylanilines

Keisuke Tokushige, Takumi Abe, Shota Asai
article en

Abstract

Abstract A concise and metal‐free procedure has been developed for the synthesis of 2‐vinylanilines. Reactions of indolines with tert ‐BuOK in DMSO afford the decorated 2‐vinylanilines in yields up to 92 %. In addition, the 2, or 3‐substituted indolines could be converted to trisubstituted alkenes. Also, the protocol can be scaled to afford gram quantities of the decorated 2‐vinylanilines.

Asian Journal of Organic ChemistryVol. 14(2)
Shujitsu University (JP), Okayama University (JP)
Openalex Percentile: Top 81%
Chemical Synthesis and Analysis
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Potassium <i>tert</i>‐Butoxide‐Mediated Ring‐Opening of Indolines: Concise Synthesis of 2‐Vinylanilines — Keisuke Tokushige, Takumi Abe, et al. · Asian Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS