Organocatalytic coupling of CO2 with a propargylic alcohol: a comprehensive study of the reaction mechanism combining in- situ ATR-IR spectroscopy and DFT calculations
[en] The metal-free coupling of propargylic alcohols with carbon dioxide catalysed by guanidine derivatives was investigated in detail through the combination of online kinetic studies by in-situ ATR-IR spectroscopy and DFT calculations. Bicyclic guanidines, namely TBD and MTBD, are effective catalysts for the conversion of 2-methyl-3-butyn-2-ol to α-methylene cyclic carbonate and oxoalkyl acyclic carbonate under mild reaction conditions. The lower selectivity of TBD in comparison with MTBD towards the formation of α-methylene cyclic carbonate was elucidated from DFT calculations and is related to the bifunctional activity (base/H-bond donor) of TBD decreasing the Gibbs free energy of the reaction path for the formation of the acyclic carbonate.
Introduction
Research center :
Center for Education and Research on Macromolecules (CERM) CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Boyaval, Amélie ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Méreau, Raphaël; University of Bordeaux, Institute of Molecular Sciences, France
Grignard, Bruno ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Tassaing, Thierry; University of Bordeaux, Institute of Molecular Sciences, France
Language :
English
Title :
Organocatalytic coupling of CO2 with a propargylic alcohol: a comprehensive study of the reaction mechanism combining in- situ ATR-IR spectroscopy and DFT calculations
Publication date :
22 March 2017
Journal title :
ChemSusChem
ISSN :
1864-5631
eISSN :
1864-564X
Publisher :
Wiley-VCH, Weinheim, Germany
Volume :
10
Issue :
6
Pages :
1241-1248
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
"Flycoat" and "CO2Green" projects
Funders :
Walloon region [BE] F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] BELSPO - Politique scientifique fédérale [BE] Conseil Général d'Aquitaine [FR]
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