Copper-Catalyzed Trifluoromethylthiolaton and Radical Cyclization of N-Phenylpent-4-Enamides to Construct SCF[sub.3]-Substituted γ-Lactams

An efficient method involving copper-catalyzed trifluoromethylthiolation and radical cyclization of N-phenylpent-4-enamides using readily available and stable AgSCF[sub.3] as the trifluoromethylthiolating reagent is described. The method enables the synthesis of a series of potential medicinally val...

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Bibliographic Details
Published in:Catalysts 2024-11, Vol.14 (11)
Main Authors: Zhang, Hanyang, Liu, Wen, Hu, Jiale, Zhang, Qian, Fang, Zeguo, Li, Dong
Format: Article
Language:English
Subjects:
Copper
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Summary:An efficient method involving copper-catalyzed trifluoromethylthiolation and radical cyclization of N-phenylpent-4-enamides using readily available and stable AgSCF[sub.3] as the trifluoromethylthiolating reagent is described. The method enables the synthesis of a series of potential medicinally valuable trifluoromethylthio-substituted γ-lactams and relative 2-oxazolidinone derivatives with broad functional group compatibility. Mechanistic investigations indicated that this reaction involved amidyl radical-initiated cascade 5-exo-trig cyclization followed by trifluoromethylthiolation, resulting in the formation of new C-N and C-S bonds.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal14110797