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Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates

The efficient conversion of CO into value‐added chemicals under metal‐free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the syn... Full description

Journal Title: ChemSusChem 22 March 2017, Vol.10(6), pp.1120-1127
Main Author: Qiu, Jikuan
Other Authors: Zhao, Yuling , Li, Zhiyong , Wang, Huiyong , Fan, Maohong , Wang, Jianji
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 1864-5631 ; E-ISSN: 1864-564X ; DOI: 10.1002/cssc.201601129
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recordid: wj10.1002/cssc.201601129
title: Efficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates
format: Article
creator:
  • Qiu, Jikuan
  • Zhao, Yuling
  • Li, Zhiyong
  • Wang, Huiyong
  • Fan, Maohong
  • Wang, Jianji
subjects:
  • Carbon Dioxide
  • Carboxylative Cyclization
  • Cyclic Carbonates
  • Ionic Liquid
  • Propargylic Alcohol
ispartof: ChemSusChem, 22 March 2017, Vol.10(6), pp.1120-1127
description: The efficient conversion of CO into value‐added chemicals under metal‐free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the synthesis of α‐alkylidene cyclic carbonates. The protic IL 1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by simple neutralization of the superbase with a weak proton donor and could efficiently promote the reactions in high yields. After the reactions, the IL was separated from the reaction mixtures by simply adding water, and then reused after drying without an observable decrease in the catalytic activity and selectivity. NMR spectroscopy and detailed density functional theory analysis were used to propose a reaction mechanism. Both the cation and anion of the IL played a key synergistic role in promoting the reaction. These findings may be useful for the rational design of novel metal‐free and recyclable routes for the reaction between CO and propargylic alcohols. ! The protic ionic liquid1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by a simple neutralization of the superbase with a weak proton donor and used to efficiently promote the chemical fixation of CO into α‐alkylidene cyclic carbonates.
language: eng
source:
identifier: ISSN: 1864-5631 ; E-ISSN: 1864-564X ; DOI: 10.1002/cssc.201601129
fulltext: fulltext
issn:
  • 1864-5631
  • 18645631
  • 1864-564X
  • 1864564X
url: Link


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titleEfficient Ionic‐Liquid‐Promoted Chemical Fixation of CO2 into α‐Alkylidene Cyclic Carbonates
creatorQiu, Jikuan ; Zhao, Yuling ; Li, Zhiyong ; Wang, Huiyong ; Fan, Maohong ; Wang, Jianji
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subjectCarbon Dioxide ; Carboxylative Cyclization ; Cyclic Carbonates ; Ionic Liquid ; Propargylic Alcohol
descriptionThe efficient conversion of CO into value‐added chemicals under metal‐free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the synthesis of α‐alkylidene cyclic carbonates. The protic IL 1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by simple neutralization of the superbase with a weak proton donor and could efficiently promote the reactions in high yields. After the reactions, the IL was separated from the reaction mixtures by simply adding water, and then reused after drying without an observable decrease in the catalytic activity and selectivity. NMR spectroscopy and detailed density functional theory analysis were used to propose a reaction mechanism. Both the cation and anion of the IL played a key synergistic role in promoting the reaction. These findings may be useful for the rational design of novel metal‐free and recyclable routes for the reaction between CO and propargylic alcohols. ! The protic ionic liquid1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by a simple neutralization of the superbase with a weak proton donor and used to efficiently promote the chemical fixation of CO into α‐alkylidene cyclic carbonates.
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descriptionThe efficient conversion of CO into value‐added chemicals under metal‐free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the synthesis of α‐alkylidene cyclic carbonates. The protic IL 1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by simple neutralization of the superbase with a weak proton donor and could efficiently promote the reactions in high yields. After the reactions, the IL was separated from the reaction mixtures by simply adding water, and then reused after drying without an observable decrease in the catalytic activity and selectivity. NMR spectroscopy and detailed density functional theory analysis were used to propose a reaction mechanism. Both the cation and anion of the IL played a key synergistic role in promoting the reaction. These findings may be useful for the rational design of novel metal‐free and recyclable routes for the reaction between CO and propargylic alcohols. ! The protic ionic liquid1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by a simple neutralization of the superbase with a weak proton donor and used to efficiently promote the chemical fixation of CO into α‐alkylidene cyclic carbonates.
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abstractThe efficient conversion of CO into value‐added chemicals under metal‐free conditions is of significant importance from the viewpoint of sustainable chemistry. In this work, ionic liquids (ILs) with different properties were used to promote the reaction between CO and propargylic alcohol for the synthesis of α‐alkylidene cyclic carbonates. The protic IL 1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by simple neutralization of the superbase with a weak proton donor and could efficiently promote the reactions in high yields. After the reactions, the IL was separated from the reaction mixtures by simply adding water, and then reused after drying without an observable decrease in the catalytic activity and selectivity. NMR spectroscopy and detailed density functional theory analysis were used to propose a reaction mechanism. Both the cation and anion of the IL played a key synergistic role in promoting the reaction. These findings may be useful for the rational design of novel metal‐free and recyclable routes for the reaction between CO and propargylic alcohols. ! The protic ionic liquid1,8‐diazabicyclo‐[5.4.0]‐7‐undecenium 2‐methylimidazolide ([DBUH][MIm]) was prepared by a simple neutralization of the superbase with a weak proton donor and used to efficiently promote the chemical fixation of CO into α‐alkylidene cyclic carbonates.
doi10.1002/cssc.201601129
pages1120-1127
date2017-03-22