Photoredox Michael addition of phenylmalononitrile onto α,β-unsaturated carboxylic acid

[Display omitted] •The direct Michael addition onto α,β-unsaturated carboxylic acid was achieved.•The Michael addition proceeded under blue-light irradiation.•The appropriate nucleophile was phenylmalononitrile.•The Michael addition proceeded onto other α,β-unsaturated carbonyl compounds. We report...

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Veröffentlicht in:Tetrahedron letters 2020-04, Vol.61 (18), p.151824, Article 151824
Hauptverfasser: Hirahama, Toshiya, Umezawa, Misaki, Shoji, Mitsuru
Format: Artikel
Sprache:eng
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Zusammenfassung:[Display omitted] •The direct Michael addition onto α,β-unsaturated carboxylic acid was achieved.•The Michael addition proceeded under blue-light irradiation.•The appropriate nucleophile was phenylmalononitrile.•The Michael addition proceeded onto other α,β-unsaturated carbonyl compounds. We report a methodology to achieve the direct Michael addition of 2-phenylmalononitrile onto α,β-unsaturated carbonyl compounds through a visible-light-induced photoredox reaction. A radical species, generated from the Michael nucleophile under blue-light irradiation in the presence of an acridinium catalyst, could connect to the β-carbon of the carbonyl substrate, to furnish γ, γ-dicyanocarboxylic acid derivatives in good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151824