Work

Copper-Catalyzed Trifluoromethylthiolaton and Radical Cyclization of N-Phenylpent-4-Enamides to Construct SCF3-Substituted γ-Lactams

Year: 2024

Type: article

Abstract: An efficient method involving copper-catalyzed trifluoromethylthiolation and radical cyclization of N-phenylpent-4-enamides using readily available and stable AgSCF3 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.

Source: Catalysts

DOI: 10.3390/catal14110797

Authors: Hanyang Zhang, Wen Liu, Jiale Hu, Qian Zhang, Zeguo Fang, Dong Li

Institution: Hubei University of Technology

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: gold

Estimated APC paid: $3,069

Funders: Hubei Provincial Department of Education, Department of Science and Technology, Hubei Provincial People's Government