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Preparation of Indolenines via Nucleophilic Aromatic Substitution


Huber, Florian; Roesslein, Joel; Gademann, Karl (2019). Preparation of Indolenines via Nucleophilic Aromatic Substitution. Organic Letters, 21(8):2560-2564.

Abstract

An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.

Abstract

An unusual aromatic substitution to access indolenines is described. 2-(2-Methoxyphenyl)acetonitrile derivatives are reacted with various alkyl and aryl Li reagents to furnish the corresponding indolenine products, constituents of natural products, and cyanine dyes such as indocyanine green. This new method was used to synthesize 41 indolenines with large functional group tolerance, and selected examples were further converted to the corresponding indolenine dyes. Key experiments provide insight into the mechanism of this nucleophilic aromatic substitution.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry
Language:English
Date:19 April 2019
Deposited On:12 Jan 2021 14:19
Last Modified:24 Jun 2024 01:42
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.9b00489
PubMed ID:30835126
Project Information:
  • : FunderSNSF
  • : Grant ID200020_163151
  • : Project TitleDirecting Neurite Outgrowth through Synthetic Natural Products
  • Content: Accepted Version