Intermolecular Radical Addition to Carbonyls Enabled by Visible Light Photoredox Initiated Hole Catalysis

Herein, we present a novel strategy for the utilization of simple carbonyl compounds, aldehydes and ketones, as intermolecular radical acceptors. The reaction is enabled by visible light photoredox initiated hole catalysis and the in situ Brønsted acid activation of the carbonyl compound. This regio...

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Veröffentlicht in:Journal of the American Chemical Society 2017-10, Vol.139 (39), p.13652-13655
Hauptverfasser: Pitzer, Lena, Sandfort, Frederik, Strieth-Kalthoff, Felix, Glorius, Frank
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, we present a novel strategy for the utilization of simple carbonyl compounds, aldehydes and ketones, as intermolecular radical acceptors. The reaction is enabled by visible light photoredox initiated hole catalysis and the in situ Brønsted acid activation of the carbonyl compound. This regioselective alkyl radical addition reaction does not require metals, ligands or additives and proceeds with a high degree of atom economy under mild conditions. The proposed mechanism is supported by both experimental and theoretical studies.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b08086