Lewis Acid Activation of Fragment-Coupling Reactions of Tertiary Carbon Radicals Promoted by Visible-Light Irradiation of EDA Complexes

The addition of tertiary carbon radicals generated from N-(acyloxy)­phthalimide esters to cyclic α,β-unsaturated ketones and lactones is markedly enhanced by the addition of substoichiometric amounts of a Ln­(OTf)3. The reaction is accomplished by irradiation with visible light in the absence of a p...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2021-02, Vol.23 (3), p.1103-1106
Hauptverfasser: Pitre, Spencer P, Allred, Tyler K, Overman, Larry E
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The addition of tertiary carbon radicals generated from N-(acyloxy)­phthalimide esters to cyclic α,β-unsaturated ketones and lactones is markedly enhanced by the addition of substoichiometric amounts of a Ln­(OTf)3. The reaction is accomplished by irradiation with visible light in the absence of a photosensitizer and is suggested to proceed by excitation of a ternary electron donor–acceptor complex between the NHPI ester, Hantzsch ester, and a Ln­(OTf)3.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00023