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

Seiya Hirao; Toshiki Yamashiro; Kyouka Kohira; Naoki Mishima; Takumi Abe

doi:10.1039/d0cc01210f

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

Seiya Hirao, Toshiki Yamashiro, Kyouka Kohira, Naoki Mishima, Takumi Abe

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

9 Citations (Scopus)

Abstract

2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed S_NAr reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceedsviaS_NAr reactions ofin situgenerated 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.

Original language	English
Pages (from-to)	5139-5142
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	38
DOIs	https://doi.org/10.1039/d0cc01210f
Publication status	Published - May 11 2020
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d0cc01210f

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title = "2,3-Dimethoxyindolines: a latent electrophile for SNAr reactions triggered by indium catalysts",

abstract = "2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed SNAr reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceedsviaSNAr reactions ofin situgenerated 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.",

author = "Seiya Hirao and Toshiki Yamashiro and Kyouka Kohira and Naoki Mishima and Takumi Abe",

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doi = "10.1039/d0cc01210f",

language = "English",

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TY - JOUR

T1 - 2,3-Dimethoxyindolines

T2 - a latent electrophile for SNAr reactions triggered by indium catalysts

AU - Hirao, Seiya

AU - Yamashiro, Toshiki

AU - Kohira, Kyouka

AU - Mishima, Naoki

AU - Abe, Takumi

N1 - Funding Information: This work was financially supported by the JSPS (KAKENHI Grant Number 16K18849 for T. A.) as a Grant-in-Aid for Young Scientists (B). Publisher Copyright: © The Royal Society of Chemistry 2020.

PY - 2020/5/11

Y1 - 2020/5/11

N2 - 2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed SNAr reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceedsviaSNAr reactions ofin situgenerated 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.

AB - 2,3-Dimethoxyindolines (DiMeOINs) have emerged as a latent electrophile in indium-catalyzed SNAr reactions. They are easily obtained from commercially available indoles and allowed access to 3-substituted indoles. The reaction proceedsviaSNAr reactions ofin situgenerated 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.

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JO - Chemical Communications

JF - Chemical Communications

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ER -

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

Abstract

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