Photoinduced C–O bond cleavage for copper-catalyzed allenyl radical cyanation

The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and par...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic Chemistry Frontiers 2022-09, Vol.9 (19), p.5259-5263
Hauptverfasser: Lu, Fu-Dong, Shu, Zhen-Cao, He, Gui-Feng, Bai, Jun-Chuan, Lu, Liang-Qiu, Xiao, Wen-Jing
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:The selective activation and transformation of C–O bonds under mild conditions is of great significance in synthetic chemistry because of the widespread existence of carbon–oxygen single bonds. In this work, allenyl radicals were generated by the photoinduced cleavage of carbon–oxygen bonds, and participated in the copper catalytic cycle, affording structurally diverse and highly significant allenyl nitriles. Both 1,3-disubstituted allenyl nitriles and trisubstituted allenyl nitriles could be assembled with moderate to good yields (24 examples, 65–95% yields) and high chemoselectivity. To prove the utility of this new methodology, an allene nitrile was converted into other valuable synthetic blocks including an allyl nitrile, alkyl nitrile and α-cyano cyclic ketone.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D2QO00938B