Radical Perfluoroalkylation of Arenes via Carbanion Intermediates

The use of sodium dithionite with perfluoroalkyl iodides under basic conditions facilitates the direct perfluoroalkylation of arenes with pendant benzylic electron-withdrawing groups. This occurs via attack of the arene on the electrophilic perfluoroalkyl radical, through the donation of electron de...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-08, Vol.86 (15), p.10903-10913
Main Authors: Hernandez, Lucas W, Gallagher, William P, Guerrero, Carlos A, Gonzalez-Bobes, Francisco, Coombs, John R
Format: Article
Language:English
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Summary:The use of sodium dithionite with perfluoroalkyl iodides under basic conditions facilitates the direct perfluoroalkylation of arenes with pendant benzylic electron-withdrawing groups. This occurs via attack of the arene on the electrophilic perfluoroalkyl radical, through the donation of electron density from a benzylic anion. The substrate scope was expanded beyond benzylic nitriles with cyclic substrates bearing electron-withdrawing groups at the benzylic positionî—¸enforcing donation of electron density to the aromatic ring and enabling attack on the perfluoroalkyl radical.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01296