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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Vydané v:	Angewandte Chemie International Edition Ročník 58; číslo 34; s. 11768 - 11773
Hlavní autori:	Ouhib, Farid, Grignard, Bruno, Van Den Broeck, Elias, Luxen, André, Robeyns, Koen, Van Speybroeck, Veronique, Jerome, Christine, Detrembleur, Christophe
Médium:	Journal Article
Jazyk:	English
Vydavateľské údaje:	WEINHEIM Wiley 19.08.2019 Wiley Subscription Services, Inc
Vydanie:	International ed. in English
Predmet:	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
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Shrnutí:	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.
Bibliografia:	These authors contributed equally to this work. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 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