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

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.

DOI: 10.1039/c6cc02284g

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Cite this paper

@article{Leifert2016RadicalP, title={Radical perfluoroalkylation - easy access to 2-perfluoroalkylindol-3-imines via electron catalysis.}, author={Dirk Leifert and Denis G Artiukhin and Johannes Neugebauer and Anzhela Galstyan and Cristian A Strassert and Armido Studer}, journal={Chemical communications}, year={2016}, volume={52 35}, pages={5997-6000} }