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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‐ amine
Author(s) -
Wang Binshen,
Luo Zhoujie,
Elageed Elnazeer H. M.,
Wu Shi,
Zhang Yongya,
Wu Xiaopei,
Xia Fei,
Zhang Guirong,
Gao Guohua
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500928
Subject(s) - ionic liquid , chemistry , catalysis , aryl , bromide , hydrogen bond , solvent , ionic bonding , organic chemistry , amine gas treating , photochemistry , combinatorial chemistry , polymer chemistry , molecule , alkyl , ion
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 CO 2 , 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 CS 2 , 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.