2,3-Dimethoxyindolines: a latent electrophile for SAr reactions triggered by indium catalysts

2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed S N Ar reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceeds via S N Ar reactions of in situ generated 3-methoxyindoles. Fo...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 38; pp. 5139 - 5142
Main Authors Hirao, Seiya, Yamashiro, Toshiki, Kohira, Kyouka, Mishima, Naoki, Abe, Takumi
Format Journal Article
LanguageEnglish
Published 12.05.2020
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Summary:2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed S N Ar reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceeds via S N Ar reactions of in situ generated 3-methoxyindoles. Formation of C2-substituted indoles was also possible utilizing the C2-nucleophilicity of DIMeOIN. Our protocol is user friendly as DiMeOIN is a bench-stable easy-to-handle crystalline reagent. An unprecedented utilization of 2,3-dimethoxyindolines (DiMeOINs) as a latent electrophile in regioselective In-catalyzed aromatic substitutions has been reported.
Bibliography:1
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10.1039/d0cc01210f
H and
NMR spectra. See DOI
Electronic supplementary information (ESI) available: Detailed experimental procedures and spectral data for all compounds, including scanned images of
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc01210f