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Thermal or Photoinduced Radical Cascade Cyclization to Access CF<sub>3</sub>/SCF<sub>3</sub>-Containing Small- and Medium-Membered-Sized <i>N</i>-Heterocycles

Kaixia Sui, Yuting Leng, Panpan Wang, Wenhao Xu, Yangjie Wu

2025The Journal of Organic Chemistry9 citationsDOI

Abstract

in two directions to access a series of trifluoromethylated five/six/seven-membered heterocycles and trifluoromethylthiolated five-membered heterocycles was developed. The model reaction was extrapolated with 74 examples, affording satisfactory yields for desired products. Further transformation and large-scale experiments were conducted and gave positive results, which paved the way to a broad application of the protocol. Additionally, the same cascade reaction of trifluoromethylation can also be realized through a photochemical approach using 4CzIPN as an organic photocatalyst at room temperature, which might provide a more mild method for constructing valuable heterocycles with biological potential.

Topics & Concepts

CascadeThermalRadical cyclizationChemistryPhotochemistryStereochemistryPhysicsThermodynamicsChromatographyFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Thermal or Photoinduced Radical Cascade Cyclization to Access CF<sub>3</sub>/SCF<sub>3</sub>-Containing Small- and Medium-Membered-Sized <i>N</i>-Heterocycles | Litcius