Abstract

Given the growing interest in utilizing CO₂ under mild and environmentally friendly conditions, this study investigates the potential of a simple and inexpensive imidazolium salt to promote the CO₂ cycloaddition of N-alkyl aziridines to generate N-alkyl oxazolidin-2-ones. Optimization of the reaction parameters revealed that 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (1) effectively catalyzes the synthesis of N-alkyl oxazolidin-2-ones in acetonitrile under mild experimental conditions (40 °C and 0.1 MPa CO₂). The bifunctional nature of 1 enabled the synthesis of various oxazolidin-2-ones in the absence of any co‑catalyst, achieving yields up to 90% and regioisomeric ratios up to 96:4. A tandem procedure has also been investigated, where N-tosyl aziridine is first formed via copper catalysis, and then converted into the corresponding oxazolidin-2-ones in the same reactor, with tetrabutylammonium chloride (TBACl) as co-catalyst. This tandem approach, while still at an early stage, has the potential to avoid the isolation and purification of the aziridine intermediate in future optimized versions.

Keywords: oxazolidin-2-ones carbon dioxide imidazolium salts tandem procedure copper

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Damiano, C.; Gallo, E.; Díaz-Requejo, M. M.; Pérez, P. J. Beilstein Arch. 2026, 202633. doi:10.3762/bxiv.2026.33.v1

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