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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| Veröffentlicht in: | Angewandte Chemie International Edition Jg. 58; H. 34; S. 11768 - 11773 |
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19.08.2019
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| 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.
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. |
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| AbstractList | 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. alpha-Alkylidene cyclic carbonates (alpha CCs) recently emerged as attractive CO2-sourced synthons for the construction of complex organic molecules. Herein, we report the transformation of alpha CCs 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. 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. 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.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. 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. |
| Author | Van Den Broeck, Elias Ouhib, Farid Grignard, Bruno Luxen, André Robeyns, Koen Detrembleur, Christophe Van Speybroeck, Veronique Jerome, Christine |
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| Cites_doi | 10.1021/acs.accounts.6b00345 10.1002/anie.201805009 10.1002/cssc.201600470 10.1002/smll.201800821 10.1002/cctc.201800063 10.1007/s41061-017-0136-5 10.1021/acs.macromol.7b01867 10.1002/cctc.201701567 10.1002/anie.201811506 10.1021/ja405114e 10.1002/ange.200901399 10.1021/acscatal.7b01422 10.1002/anie.201704467 10.1021/acs.orglett.9b00156 10.1039/c4gc01959h 10.1039/c7cy00438a 10.1021/acsomega.6b00407 10.1002/anie.200901399 10.1039/c7ra08958a 10.1021/acs.chemrev.5b00355 10.1021/cr400725x 10.1039/c5py00773a 10.1039/c5sc00040h 10.1021/cs5018997 10.1021/op500155f 10.1039/b707893e 10.1016/j.cogsc.2016.11.005 10.1002/anie.201805200 10.1021/cr500235v 10.1002/adsc.201801215 10.1039/c7gc00276a 10.1039/c5gc01870f 10.1039/c7gc02560b 10.1002/cssc.201601524 10.1016/j.progpolymsci.2017.12.004 |
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| Keywords | 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 |
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| Snippet | α‐Alkylidene cyclic carbonates (αCCs) recently emerged as attractive CO2‐sourced synthons for the construction of complex organic molecules. Herein, we report... alpha-Alkylidene cyclic carbonates (alpha CCs) recently emerged as attractive CO2-sourced synthons for the construction of complex organic molecules. Herein,... α-Alkylidene cyclic carbonates (αCCs) recently emerged as attractive CO2 -sourced synthons for the construction of complex organic molecules. Herein, we report... alpha-alkylidene cyclic carbonates (aCCs) recently emerged as attractive CO2-sourced synthons for the construction of complex organic molecules. Herein, we... |
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| SubjectTerms | 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 |
| Title | A Switchable Domino Process for the Construction of Novel CO2‐Sourced Sulfur‐Containing Building Blocks and Polymers |
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