Organocatalytic coupling of CO2 with a propargylic alcohol: a comprehensive study of the reaction mechanism combining in- situ ATR-IR spectroscopy and DFT calculations

Boyaval, Amélie; Méreau, Raphaël; Grignard, Bruno; Detrembleur, Christophe; Jérôme, Christine; Tassaing, Thierry

doi:10.1002/cssc.201601524

Article (Scientific journals)

Organocatalytic coupling of CO2 with a propargylic alcohol: a comprehensive study of the reaction mechanism combining in- situ ATR-IR spectroscopy and DFT calculations

Boyaval, Amélie; Méreau, Raphaël; Grignard, Bruno et al.

2017 • In ChemSusChem, 10 (6), p. 1241-1248

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/204164

DOI
10.1002/cssc.201601524

PubMed
27925442

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Keywords :

supercritical carbon dioxide

Abstract :

[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/Unit :

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 :

Issue :

Pages :

1241-1248

Peer reviewed :

Peer Reviewed verified by ORBi

Name of the research project :

"Flycoat" and "CO2Green" projects

Funders :

Walloon region
F.R.S.-FNRS - Fonds de la Recherche Scientifique
BELSPO - Politique scientifique fédérale
Conseil Général d'Aquitaine

Available on ORBi :

since 09 December 2016

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