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Bypassing the Inertness of Aziridine/CO2 Systems to Access 5-Aryl-2-Oxazolidinones: Catalyst-Free Synthesis Under Ambient Conditions

preprint
revised on 12.08.2020 and posted on 13.08.2020 by Giulio Bresciani, Emanuele Antico, Gianluca Ciancaleoni, Stefano Zacchini, Guido Pampaloni, Fabio Marchetti
The development of sustainable synthetic routes to access valuable oxazolidinones via CO2 fixation is an active research area, and the aziridine/carbon dioxide coupling has aroused a considerable interest. This reaction is featured by a high activation barrier, so to require a catalytic system, and may present some other critical issues. Here, we describe the straightforward gram-scale synthesis of a series of 5-​aryl-​2-oxazolidinones at ambient temperature and atmospheric CO2 pressure, in the absence of any catalyst/co-catalyst. The key to this innovative procedure consists in the direct transfer of the pre-formed amine/CO2 adduct (carbamate) to common aziridine precursors (dimethylsulfonium salts), replacing the classical sequential addition of amine (intermediate isolation of aziridine) and then CO2. The reaction mechanism has been investigated by NMR studies and DFT calculations applied to model cases.

History

Email Address of Submitting Author

fabio.marchetti1974@unipi.it

Institution

University of Pisa

Country

Italy

ORCID For Submitting Author

0000-0002-3683-8708

Declaration of Conflict of Interest

The authors declare no conflicts of interest

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