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Synthesis of Functionalized Cyclic Carbonates by One‐Pot Reactions of Carbon Dioxide, Epibromohydrin, and Phenols, Thiophenols, or Carboxylic Acids Catalyzed by Ionic Liquids
Author(s) -
Wu Shi,
Zhang Yongya,
Wang Binshen,
Elageed Elnazeer H. M.,
Ji Liangzheng,
Wu Haihong,
Gao Guohua
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601315
Subject(s) - chemistry , catalysis , ionic liquid , thioether , carboxylation , bromide , organic chemistry , ether , phenols , alkoxide , medicinal chemistry
The one‐pot reactions of CO 2 , epibromohydrin, and phenols, thiophenols, or carboxylic acids catalyzed by 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide were investigated. Three kinds of cyclic carbonates with ether, thioether, or ester groups were synthesized under mild reaction conditions in good‐to‐high yields. Reaction‐mechanism studies indicated that the proton exchange between the alkoxide formed through the ring‐opening reaction of epibromohydrin with 1‐bromo‐3‐phenoxy‐2‐propanol plays a crucial role in this synthetic route. The catalyst 1‐butyl‐3‐[(3‐hydroxyphenyl)methyl]imidazolium bromide was transformed to the corresponding cyclic‐carbonate‐functionalized ionic liquid during the reaction. This transformation did not affect its catalytic performance in the reaction.