Synthesis of Functionalized Cyclic Carbonates by One‐Pot Reactions of Carbon Dioxide, Epibromohydrin, and Phenols, Thiophenols, or Carboxylic Acids Catalyzed by Ionic Liquids. Issue 3 (24th January 2017)

• Record Type: Journal Article
• Authors: Wu, Shi; Zhang, Yongya; Wang, Binshen; Elageed, Elnazeer H. M.; Ji, Liangzheng; Wu, Haihong; Gao, Guohua
• Is Part Of: European journal of organic chemistry. Issue 3(2017)
• Page Start: 753
• Page End: 759
• Publication Date: 2017-01-24
• Subjects: Carbon dioxide -- Oxygen heterocycles -- Ionic liquids -- Cyclic carbonates -- Synthesis design; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601315
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The one‐pot reactions of CO2, 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. Abstract : A procedure for the synthesis of functionalized cyclic carbonates from the one‐pot reactions of CO2, epibromohydrin, and phenols, thiophenols, or carboxylic acids catalyzed by ionic liquids is developed. Under mild reaction conditions, 28 functionalized cyclic carbonates, including 15 new compounds, are synthesized in good‐to‐high yields. A proton exchange plays a crucial role in the reaction.