We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
In Situ Generated Zinc(II) Catalyst for Incorporation of CO<sub>2</sub> into 2-Oxazolidinones with Propargylic Amines at Atmospheric Pressure.
- Authors
Liu, Xi; Wang, Mei ‐ Yan; Wang, Si ‐ Yuan; Wang, Qi; He, Liang ‐ Nian
- Abstract
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. 13C 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.
- Subjects
HETEROCYCLIC compounds; CARBON dioxide; OXAZOLIDONES; CARBON-carbon bonds synthesis; ZINC catalysts; PROPARGYLAMINES
- Publication
ChemSusChem, 2017, Vol 10, Issue 6, p1210
- ISSN
1864-5631
- Publication type
Article
- DOI
10.1002/cssc.201601469