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Issue 35, 2016
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Radical perfluoroalkylation – easy access to 2-perfluoroalkylindol-3-imines via electron catalysis

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Abstract

Arylisonitriles (2 equivalents) react with alkyl and perfluoroalkyl radicals to form 2-alkylated indole-3-imines via two sequential additions to the isonitrile moiety followed by homolytic aromatic substitution. The three component reaction comprises three C–C bond formations. The endocyclic imine functionality in the products is more reactive in follow up chemistry and hydrolysis of the exocyclic imine leads to 3-oxindoles that show fluorescence properties.

Graphical abstract: Radical perfluoroalkylation – easy access to 2-perfluoroalkylindol-3-imines via electron catalysis

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Supplementary files

Article information


Submitted
15 Mar 2016
Accepted
31 Mar 2016
First published
31 Mar 2016

This article is Open Access

Chem. Commun., 2016,52, 5997-6000
Article type
Communication

Radical perfluoroalkylation – easy access to 2-perfluoroalkylindol-3-imines via electron catalysis

D. Leifert, D. G. Artiukhin, J. Neugebauer, A. Galstyan, C. A. Strassert and A. Studer, Chem. Commun., 2016, 52, 5997
DOI: 10.1039/C6CC02284G

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