Metal Acetylacetonates as Robust Catalysts for the Synthesis of Oxazolidinone from CO₂ and Aziridine Under Atmospheric Pressure

Abstract

Metal acetylacetonates, a type of readily synthesized or commercially available metal complex, were demonstrated to be robust catalysts for the synthesis of oxazolidinone from CO₂ and aziridine under condition of atmospheric pressure and mild temperature, exhibiting high chemo- and regio-selectivity. Tetrabutylammonium halides were employed as cocatalysts in the reaction, and it was believed that the reaction activity was influenced by a balance of anions’ two abilities, namely their nucleophilicity in ring-opening of aziridines and their leaving capacity in ring-closing of intermediate carbamate salts to form oxazolidinones. Notably, higher nucleophilicity of these anions resulted in increased formation of dimers, which served as by-products of the reaction. The study of mechanism suggested that there should be an alternative pathway involving CO₂ derivative acting as a nucleophile during the ring-opening process, and this pathway could not be ignored when conventional nucleophiles, such as tetrabutylammonium halides are absent.

Keywords

Metal acetylacetonate / Carbon dioxide / Aziridine / Oxazolidinone / Atmospheric pressure

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