Tf2O‑Mediated Tandem Reaction of Enaminones for the Synthesis of Functionalized Conjugated-Enals/β-Naphthalaldehydes

A highly efficient and regioselective method for constructing functionalized conjugated enals via the Tf2O-mediated tandem reaction of enaminones with thiophenols has been described. Chain products with excellent stereoselectivity could be obtained through substrate regulation. Additionally, a feasi...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of organic chemistry 2024-01, Vol.89 (1), p.373-378
Hauptverfasser:	Zhang, Changyuan, Lin, Jianping, Wang, Li, Mei, Yingxuan, Wang, Lanjing, Xie, Yuqing, Lu, Yu, Tian, Jiakai, Wang, Wei, Chen, Lulu, Guo, Mengping, Zhou, Cailong
Format:	Artikel
Sprache:	eng
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	A highly efficient and regioselective method for constructing functionalized conjugated enals via the Tf2O-mediated tandem reaction of enaminones with thiophenols has been described. Chain products with excellent stereoselectivity could be obtained through substrate regulation. Additionally, a feasible method for synthesizing β-naphthalaldehydes through PhSO2Na/DABCO promoting hydrogen atom transfer process has also been reported here. Mechanism studies have shown that 2-formyl vinyl triflate 8 and sulfonylated enal 9 were the key intermediates in this process.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/acs.joc.3c02108