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

Author
Organization
Abstract
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.
Keywords
General Chemistry, Catalysis

Citation

Please use this url to cite or link to this publication:

MLA
Ouhib, Farid et al. “A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers.” Angewandte Chemie International Edition (2019): 11768–11773. Print.
APA
Ouhib, F., Grignard, B., Luxen, A., Robeyns, K., Van Speybroeck, V., Jerome, C., Detrembleur, C., et al. (2019). A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers. Angewandte Chemie International Edition, 11768–11773.
Chicago author-date
Ouhib, Farid, Bruno Grignard, André Luxen, Koen Robeyns, Veronique Van Speybroeck, Christine Jerome, Christophe Detrembleur, and Elias Van Den Broeck. 2019. “A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers.” Angewandte Chemie International Edition: 11768–11773.
Chicago author-date (all authors)
Ouhib, Farid, Bruno Grignard, André Luxen, Koen Robeyns, Veronique Van Speybroeck, Christine Jerome, Christophe Detrembleur, and Elias Van Den Broeck. 2019. “A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers.” Angewandte Chemie International Edition: 11768–11773.
Vancouver
1.
Ouhib F, Grignard B, Luxen A, Robeyns K, Van Speybroeck V, Jerome C, et al. A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers. Angewandte Chemie International Edition. 2019;11768–73.
IEEE
[1]
F. Ouhib et al., “A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers,” Angewandte Chemie International Edition, pp. 11768–11773, 2019.
@article{8625325,
  abstract     = {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.},
  author       = {Ouhib, Farid and Grignard, Bruno and Luxen, André and Robeyns, Koen and Van Speybroeck, Veronique and Jerome, Christine and Detrembleur, Christophe and Van Den Broeck, Elias},
  issn         = {1433-7851},
  journal      = {Angewandte Chemie International Edition},
  keywords     = {General Chemistry,Catalysis},
  language     = {eng},
  pages        = {11768--11773},
  title        = {A Switchable Domino Process for the Construction of Novel CO2-Sourced Sulfur-Containing Building Blocks and Polymers},
  url          = {http://dx.doi.org/10.1002/anie.201905969},
  year         = {2019},
}

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