DBU and DBU‐Derived Ionic Liquid Synergistic Catalysts for the Conversion of Carbon Dioxide/Carbon Disulfide to 3‐Aryl‐2‐oxazolidinones/[1, 3]Dithiolan‐2‐ylidenephenyl‐ amine1. Issue 4 (21st January 2016)

• Record Type: Journal Article
• Authors: Wang, Binshen; Luo, Zhoujie; Elageed, Elnazeer H. M.; Wu, Shi; Zhang, Yongya; Wu, Xiaopei; Xia, Fei; Zhang, Guirong; Gao, Guohua
• Is Part Of: ChemCatChem. Volume 8:Issue 4(2016)
• Page Start: 830
• Page End: 838
• Publication Date: 2016-01-21
• Subjects: carbon dioxide fixation -- cooperative effects -- density functional calculations -- ionic liquids -- reaction mechanisms; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201500928
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: An intermolecular synergistic catalytic combination of 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) and a DBU‐derived bromide ionic liquid has been developed for the conversion of CO2, epoxides, and amines under metal‐ and solvent‐free conditions. Various 3‐aryl‐2‐oxazolidinones are produced in moderate to excellent yields within a short reaction time. NMR spectroscopy and DFT calculations demonstrate that DBU as a hydrogen bond acceptor and the ionic liquid as a hydrogen bond donor activate the substrates cooperatively by inducing hydrogen bonds to promote the reaction effectively. Based on these results, a possible reaction mechanism on the synergistic catalysis of DBU and the ionic liquid is proposed. In addition, the reaction of CS2, ethylene oxide, and aniline catalyzed by the combination of DBU and the DBU‐derived ionic liquid also proceeds smoothly, which opens a hitherto unreported route to [1, 3]dithiolan‐2‐ylidenephenylamine in a straightforward way. Abstract : Simply synergy : The combination of the organic superbase 1, 8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) and the superbase‐derived bromide ionic liquid HDBUBr exhibits intermolecular synergistic catalysis for the reaction of CO2, epoxides, and amines. Various 3‐aryl‐2‐oxazolidinones are synthesized in moderate to excellent yields. NMR spectroscopy and DFT calculations are used to demonstrate that the synergistic catalysts activate the substrates by inducing hydrogen bonds cooperatively.