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A Switchable Domino Process for the Construction of Novel CO 2 ‐Sourced Sulfur‐Containing Building Blocks and Polymers
Author(s) -
Ouhib Farid,
Grignard Bruno,
Van Den Broeck Elias,
Luxen André,
Robeyns Koen,
Van Speybroeck Veronique,
Jerome Christine,
Detrembleur Christophe
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201905969
Subject(s) - synthon , sulfur , polymer , substrate (aquarium) , domino , raw material , chemistry , atom economy , nanotechnology , combinatorial chemistry , organic chemistry , materials science , catalysis , oceanography , geology
α‐Alkylidene cyclic carbonates (αCCs) recently emerged as attractive CO 2 ‐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 CO 2 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.