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A Switchable Domino Process for the Construction of Novel CO2 -Sourced Sulfur-Containing Building Blocks and Polymers
Farid Ouhib1, Bruno Grignard1, Elias Van Den Broeck2
1Center for Education and Research on Macromolecules (CERM), CESAM Research Unit, University of Liège, Sart-Tilman B6a, 4000, Liege, Belgium.
Abstract:
α-Alkylidene cyclic carbonates (αCCs) recently emerged as attractive CO2 -sourced synthons for the construction of complex organic molecules. Herein, we report the transformation of αCCs 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 and 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.
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