In Situ Generated Zinc(II) Catalyst for Incorporation of CO2 into 2-Oxazolidinones with Propargylic Amines at Atmospheric Pressure.

Xi Liu, Mei-Yan Wang, Si-Yuan Wang, Qi Wang, Liang-Nian He

ChemSusChem 2017 Mar 22

filter terms:

Incorporation of CO2 into heterocyclic compounds (i.e., 2-oxazolidinones) under mild conditions, especially at atmospheric pressure still remains challenging. The mononuclear ZnII complex ZnCl2 (TBD)2 , where TBD=1,5,7-triazabicyclo[4.4.0]dec-5-ene, in this study was demonstrated as a robust catalyst for the carboxylative cyclization of propargylic amines with CO2 to exclusively afford various 2-oxazolidinones in excellent yields. Notably, the ZnII catalytic species is readily generated in situ from ZnCl2 and TBD without pre-preparation and further isolation. Such a CO2 fixation protocol could proceed smoothly under atmospheric pressure at mild temperature in an atom economic and environmentally benign manner. 13 C NMR and control experiments were performed to explore the possible interaction between ZnII and the carbon-carbon triple bond of propargylic amine. The dual catalytic role of the Zn catalyst to enhance O-nucleophilicity of the carbamate anion intermediate and activate the carbon-carbon triple bond is proposed based on mechanistic investigations. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Xi Liu, Mei-Yan Wang, Si-Yuan Wang, Qi Wang, Liang-Nian He. In Situ Generated Zinc(II) Catalyst for Incorporation of CO2 into 2-Oxazolidinones with Propargylic Amines at Atmospheric Pressure. ChemSusChem. 2017 Mar 22;10(6):1210-1216