[en] alpha-alkylidene cyclic carbonates (aCCs) recently emerged as attractive CO2-sourced synthons for the construction of complex organic molecules. Herein, we report the transformation of aCCs into novel families of sulfur-containing compounds by organocatalyzed chemoselective addition of thiols, following a domino process that is switched on/off depending on the desired product. The process is extremely fast, versatile in substrate scope, provides selectively linear thiocarbonates or elusive tetrasubstituted ethylene carbonates with high yields following a 100% atom economy reaction, and valorizes CO2 as a renewable feedstock. It is also exploited to produce a large diversity of unprecedented functional polymers. It constitutes a robust platform for the design of new sulfur-containing organic synthons and important families of polymers.
Research Center/Unit :
CESAM - Complex and Entangled Systems from Atoms to Materials - ULiège Center for Education and Research on Macromolecules (CERM), Belgium
Disciplines :
Chemistry Materials science & engineering
Author, co-author :
Ouhib, Farid ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium
Grignard, Bruno ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium
Van den Broeck, Elias; Ghent University, Center for Molecular Modeling, Belgium > ,
Luxen, André ; Univeristy of Liège (ULiège), GIGA – CRC in vivo Imaging, Belgium
Robeyns, Koen; Université Catholique de Louvain (UCL), Institute of Condensed Matter and Nanosciences (IMCN), Belgium
Van Speybroeck, Véronique; Ghent University, Center for Molecular Modeling, Belgium
Jérôme, Christine ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium
Detrembleur, Christophe ; University of Liège (ULiège), Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM), Belgium
Language :
English
Title :
A switchable domino process for the construction of novel CO2- sourced sulfur-containing building blocks and polymers
Publication date :
19 August 2019
Journal title :
Angewandte Chemie International Edition
ISSN :
1433-7851
eISSN :
1521-3773
Publisher :
Wiley, Weinheim, Germany
Volume :
58
Issue :
34
Pages :
11768-11773
Peer reviewed :
Peer Reviewed verified by ORBi
Name of the research project :
The Excellence of Science (EOS) Program in the frame of the NECOPOL Project
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen [BE] EOS - The Excellence Of Science Program [BE]