Transformation of atmospheric CO2 catalyzed by protic ionic liquids: efficient synthesis of 2-oxazolidinones

Jiayin Hu; Jun Ma; Qinggong Zhu; Zhaofu Zhang; Congyi Wu; Buxing Han

doi:10.1002/anie.201411969

Transformation of atmospheric CO2 catalyzed by protic ionic liquids: efficient synthesis of 2-oxazolidinones

Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5399-403. doi: 10.1002/anie.201411969. Epub 2015 Mar 3.

Authors

Jiayin Hu¹, Jun Ma, Qinggong Zhu, Zhaofu Zhang, Congyi Wu, Buxing Han

Affiliation

¹ Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Colloid and Interface and Thermodynamics Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China).

PMID: 25735887
DOI: 10.1002/anie.201411969

Abstract

Protic ionic liquids (PILs), such as 1,8-diazabicyclo[5.4.0]-7-undecenium 2-methylimidazolide [DBUH][MIm], can catalyze the reaction of atmospheric CO2 with a broad range of propargylic amines to form the corresponding 2-oxazolidinones. The products are formed in high yields under mild, metal-free conditions. The cheaper and greener PILs can be easily recycled and reused at least five times without a decrease in the catalytic activity and selectivity. A reaction mechanism was proposed on the basis of a detailed DFT study which indicates that both the cation and anion of the PIL play key synergistic roles in accelerating the reaction.

Keywords: carbon dioxide fixation; density functional calculations; heterocycles; ionic liquids; reaction mechanisms.