Turning carbon dioxide into dialkyl carbonates through guanidinium-assisted SN2 N2 ion-pair process
- Author
- Juliette Delcorps, Kuber Singh Rawat (UGent) , Mathilde Wells, Emna Ben Ayed, Bruno Grignard, Christophe Detrembleur, Bertrand Blankert, Pascal Gerbaux, Veronique Van Speybroeck (UGent) and Olivier Coulembier
- Organization
- Project
- Abstract
- The synthesis of dialkyl carbonates, versatile compounds with applications in organic synthesis, pharmaceuticals, and polymers, has attracted considerable attention due to their environmentally benign nature. Here, we describe the selective bimolecular nucleophilic substitution (SN2) N 2) reaction between primary and secondary alkyl iodides with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-based carbon dioxide-binding organic liquids. We show that TBD is a great candidate for bulk carbon dioxide and alcohol binding at 100 degrees C. degrees C. TBDbased carbonate salts are selective for SN2 N 2 processes, allowing them to work with highly reactive alkyl iodide while eliminating unwanted base quaternization either in acetonitrile or in bulk at both 21 degrees C degrees C and 65 degrees C. degrees C. The high reactivity of these TBD-based carbon dioxide-binding organic liquids toward backside SN2 N 2 processes at low temperature is explained by the presence of the TBD.H+ + guanidinium, revealing a unique metal-free cation-assisted SN2 N 2 ion-pair process.
- Keywords
- METAL-FREE SYNTHESIS, DIMETHYL CARBONATE, ORGANIC CARBONATES, S(N)2 REACTIONS, CO2, AMINOLYSIS, CATALYSTS, LIQUIDS, TEMPERATURE, SOLUBILITY
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01J5X1R47TQE5ACTC71XNMADSW
- MLA
- Delcorps, Juliette, et al. “Turning Carbon Dioxide into Dialkyl Carbonates through Guanidinium-Assisted SN2 N2 Ion-Pair Process.” CELL REPORTS PHYSICAL SCIENCE, vol. 5, no. 7, 2024, doi:10.1016/j.xcrp.2024.102057.
- APA
- Delcorps, J., Singh Rawat, K., Wells, M., Ben Ayed, E., Grignard, B., Detrembleur, C., … Coulembier, O. (2024). Turning carbon dioxide into dialkyl carbonates through guanidinium-assisted SN2 N2 ion-pair process. CELL REPORTS PHYSICAL SCIENCE, 5(7). https://doi.org/10.1016/j.xcrp.2024.102057
- Chicago author-date
- Delcorps, Juliette, Kuber Singh Rawat, Mathilde Wells, Emna Ben Ayed, Bruno Grignard, Christophe Detrembleur, Bertrand Blankert, Pascal Gerbaux, Veronique Van Speybroeck, and Olivier Coulembier. 2024. “Turning Carbon Dioxide into Dialkyl Carbonates through Guanidinium-Assisted SN2 N2 Ion-Pair Process.” CELL REPORTS PHYSICAL SCIENCE 5 (7). https://doi.org/10.1016/j.xcrp.2024.102057.
- Chicago author-date (all authors)
- Delcorps, Juliette, Kuber Singh Rawat, Mathilde Wells, Emna Ben Ayed, Bruno Grignard, Christophe Detrembleur, Bertrand Blankert, Pascal Gerbaux, Veronique Van Speybroeck, and Olivier Coulembier. 2024. “Turning Carbon Dioxide into Dialkyl Carbonates through Guanidinium-Assisted SN2 N2 Ion-Pair Process.” CELL REPORTS PHYSICAL SCIENCE 5 (7). doi:10.1016/j.xcrp.2024.102057.
- Vancouver
- 1.Delcorps J, Singh Rawat K, Wells M, Ben Ayed E, Grignard B, Detrembleur C, et al. Turning carbon dioxide into dialkyl carbonates through guanidinium-assisted SN2 N2 ion-pair process. CELL REPORTS PHYSICAL SCIENCE. 2024;5(7).
- IEEE
- [1]J. Delcorps et al., “Turning carbon dioxide into dialkyl carbonates through guanidinium-assisted SN2 N2 ion-pair process,” CELL REPORTS PHYSICAL SCIENCE, vol. 5, no. 7, 2024.
@article{01J5X1R47TQE5ACTC71XNMADSW,
abstract = {{The synthesis of dialkyl carbonates, versatile compounds with applications in organic synthesis, pharmaceuticals, and polymers, has attracted considerable attention due to their environmentally benign nature. Here, we describe the selective bimolecular nucleophilic substitution (SN2) N 2) reaction between primary and secondary alkyl iodides with 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-based carbon dioxide-binding organic liquids. We show that TBD is a great candidate for bulk carbon dioxide and alcohol binding at 100 degrees C. degrees C. TBDbased carbonate salts are selective for SN2 N 2 processes, allowing them to work with highly reactive alkyl iodide while eliminating unwanted base quaternization either in acetonitrile or in bulk at both 21 degrees C degrees C and 65 degrees C. degrees C. The high reactivity of these TBD-based carbon dioxide-binding organic liquids toward backside SN2 N 2 processes at low temperature is explained by the presence of the TBD.H+ + guanidinium, revealing a unique metal-free cation-assisted SN2 N 2 ion-pair process.}},
articleno = {{102057}},
author = {{Delcorps, Juliette and Singh Rawat, Kuber and Wells, Mathilde and Ben Ayed, Emna and Grignard, Bruno and Detrembleur, Christophe and Blankert, Bertrand and Gerbaux, Pascal and Van Speybroeck, Veronique and Coulembier, Olivier}},
issn = {{2666-3864}},
journal = {{CELL REPORTS PHYSICAL SCIENCE}},
keywords = {{METAL-FREE SYNTHESIS,DIMETHYL CARBONATE,ORGANIC CARBONATES,S(N)2 REACTIONS,CO2,AMINOLYSIS,CATALYSTS,LIQUIDS,TEMPERATURE,SOLUBILITY}},
language = {{eng}},
number = {{7}},
pages = {{22}},
title = {{Turning carbon dioxide into dialkyl carbonates through guanidinium-assisted SN2 N2 ion-pair process}},
url = {{http://doi.org/10.1016/j.xcrp.2024.102057}},
volume = {{5}},
year = {{2024}},
}
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