Michael addition catalyzed by difluorotris(pentafluoroethyl)phosphorane

•(C2F5)3PF2 easy to handle non-metal based strong Lewis acid.•(C2F5)3PF2 efficiently catalyzes Michael addition reaction under mild conditions.•The products are isolated in high to moderate yields. Difluorotris(pentafluoroethyl)phosphorane, (C2F5)3PF2, was found to be an active catalyst for the Mich...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2016-02, Vol.182, p.22-27
Main Authors: Bittner, Bożena, Koppe, Karsten, Frank, Walter, Ignat’ev, Nikolai
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Difluorotris(pentafluoroethyl)phosphorane
Fluorine
Formations
Ketones
Lewis acid
Michael addition
Michael reaction
Unsaturated
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Summary:•(C2F5)3PF2 easy to handle non-metal based strong Lewis acid.•(C2F5)3PF2 efficiently catalyzes Michael addition reaction under mild conditions.•The products are isolated in high to moderate yields. Difluorotris(pentafluoroethyl)phosphorane, (C2F5)3PF2, was found to be an active catalyst for the Michael addition reaction of 1,3-β-diketones or β-ketoesters (Michael donors) and linear or cyclic unsaturated ketones (Michael acceptors). The reaction proceeds under mild conditions with low catalyst loading and results in the formation of the Michael addition products in moderate to high yields. The developed protocol does not require the use of a base for the in situ generation of a carbanion (Michael donor).
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2015.11.007