[en] We have explored the domino reaction between propargylic alcohols, carbon dioxide and various alcohols with the double objective to prepare oxo-alkylcarbonates with a high yield and selectivity under mild conditions and to extend the process to the synthesis of phosgene-free polycarbonates. We first searched for a common catalytic system that was highly selective for the two reactions involved in the domino process, i.e. the cycloaddition of CO2 to propargylic alcohol to yield α-alkylidene cyclic carbonate (αCC), and the alcoholysis of αCC to furnish the oxo-alkylcarbonate. Kinetics studies monitored by operando IR spectroscopy and supported by 1H-NMR analyses and DFT modeling have permitted to identify an efficient binary catalytic system composed of a combination of tetrabutylammonium phenolate [TBA][OPh] and silver iodide (AgI) (or copper iodide (CuI)) and to understand its action mode. The [TBA][OPh]/AgI catalytic system (5 mol%) was then successfully implemented for the selective preparation of a range of oxo-alkylcarbonates by the domino reaction with alcohols and propargylic alcohols of different structures. Most of these oxo-alkylcarbonates were produced at a high yield (≧ 97 %) under mild operating conditions, i.e. at 60 °C and 1 bar of CO2. The one-pot synthesis of various poly(β-oxocarbonate)s from bis(propargylic alcohol)s, diols and CO2 was finally investigated and the best operating conditions ([TBA][OPh]/AgI (10 mol%), 60 °C, 15 bar) afforded polycarbonate oligomers with weight-average molar masses of 4,300 g/mol. Although the system should be optimized to produce longer polymer chains, this process offers a new phosgene-free alternative to the synthesis of functional polycarbonates (poly(oxo-carbonate)s) under mild conditions.
Research Center/Unit :
Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit Research Unit, Center for Education and Research on Macromolecules (CERM)
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Ngassam Tounzoua, Charlène ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Grignard, Bruno ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Brege, Antoine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Tassaing, Thierry; University of Bordeaux, CNRS, Institute of Molecular Sciences, Talence, France
Méreau, Raphaël; University of Bordeaux, CNRS, Institute of Molecular Sciences, Talence, France
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM) Research Unit, Center for Education and Research on Macromolecules (CERM), Belgium
Language :
English
Title :
A catalytic domino approach towards oxo-alkyl carbonates and polycarbonates from CO2, propargylic alcohols and (mono- and di-) alcohols
Publication date :
06 July 2020
Journal title :
ACS Sustainable Chemistry and Engineering
eISSN :
2168-0485
Publisher :
American Chemical Society, Washington, United States - District of Columbia
Volume :
8
Issue :
26
Pages :
9698-9710
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture EOS - The Excellence Of Science Program FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
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