A Switchable Domino Process for the Construction of Novel CO2‐Sourced Sulfur‐Containing Building Blocks and Polymers

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition Vol. 58; no. 34; pp. 11768 - 11773
Main Authors: Ouhib, Farid, Grignard, Bruno, Van Den Broeck, Elias, Luxen, André, Robeyns, Koen, Van Speybroeck, Veronique, Jerome, Christine, Detrembleur, Christophe
Format: Journal Article
Language:English
Published: WEINHEIM Wiley 19.08.2019
Wiley Subscription Services, Inc
Edition:International ed. in English
Subjects:
Alkylidene
Atom economy
Carbon dioxide
Carbonates
Chemistry
Chemistry, Multidisciplinary
Chimie
Construction
cyclic carbonate
domino process
Engineering, computing & technology
Ingénierie, informatique & technologie
Materials science & engineering
Organic chemistry
organocatalysis
Physical Sciences
Physical, chemical, mathematical & earth Sciences
Physique, chimie, mathématiques & sciences de la terre
polymerization
Polymers
Science & Technology
Science des matériaux & ingénierie
step-growth polymerization
Substrates
Sulfur
supercritical carbon dioxide
synthetic methods
Thiols
TRANSFORMATION
carbon dioxide
polymerization
domino process
DIOXIDE
CO2
EFFICIENT SYNTHESIS
HIGH REFRACTIVE-INDEX
CATALYST
organocatalysis
PROPARGYLIC ALCOHOLS
ALKYLIDENE CYCLIC CARBONATES
SELECTIVE SYNTHESIS
COPOLYMERIZATION
synthetic methods
ISSN:1433-7851, 1521-3773, 1521-3773
Online Access:Get full text
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Summary: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. High atom economy: Linear thiocarbonates and elusive tetrasubstituted ethylene carbonates are accessible in high yields from the organocatalyzed chemoselective addition of thiols to α‐alkylidene cyclic carbonates thanks to a switchable domino process. This robust synthetic method is also exploited for the facile construction of a large diversity of unprecedented sulfur‐containing polymers.
Bibliography:These authors contributed equally to this work.
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The Excellence of Science (EOS) Program in the frame of the NECOPOL Project
scopus-id:2-s2.0-85069858989
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201905969