US EPA

7423337 

Journal Article 

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

Liu, X; Wang, MY; Wang, SY; Wang, Q; He, LN; , 

2017 

Yes 

ChemSusChem
ISSN: 1864-5631
EISSN: 1864-564X 

Wiley-VCH Verlag 

10 

6 

1210-1216 

English 

27860345 

10.1002/cssc.201601469 

WOS:000398182800022 

http://doi.wiley.com/10.1002/cssc.201601469
Exit
 

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. 

carbon dioxide; carboxylative cyclization; catalysis; dual activation; zinc; Amines; Atmospheric pressure; Carbon dioxide; Catalysis; Catalysts; Cyclization; Zinc; Zinc chloride; 1 ,5 ,7-triazabicyclo[4.4.0]dec-5-ene; Catalytic species; Control experiments; Dual activation; Environmentally benign; Heterocyclic compound; Mild temperatures; Propargylic amines; Chlorine compounds; alkyne; amine; carbon dioxide; oxazolidinone derivative; zinc; atmospheric pressure; catalysis; chemistry; cyclization; Alkynes; Amines; Atmospheric Pressure; Carbon Dioxide; Catalysis; Cyclization; Oxazolidinones; Zinc