TY - JOUR
T1 - 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
AU - Wang, Binshen
AU - Luo, Zhoujie
AU - Elageed, Elnazeer H.M.
AU - Wu, Shi
AU - Zhang, Yongya
AU - Wu, Xiaopei
AU - Xia, Fei
AU - Zhang, Guirong
AU - Gao, Guohua
N1 - Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/2/18
Y1 - 2016/2/18
N2 - 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.
AB - 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.
KW - carbon dioxide fixation
KW - cooperative effects
KW - density functional calculations
KW - ionic liquids
KW - reaction mechanisms
UR - https://www.scopus.com/pages/publications/84968368121
U2 - 10.1002/cctc.201500928
DO - 10.1002/cctc.201500928
M3 - 文章
AN - SCOPUS:84968368121
SN - 1867-3880
VL - 8
SP - 830
EP - 838
JO - ChemCatChem
JF - ChemCatChem
IS - 4
ER -