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Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide

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2022
Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide (16.19Mb)
Authors
Božić, Bojan
Lađarević, Jelena
Petković, Miloš
Mijin, Dušan
Stavber, Stojan
Article (Published version)
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Abstract
The susceptibility of the carbonyl group towards nucleophilic attack affords the construction of various organic compounds. Thus, investigations of carbonyl activation applying greener methodologies are highly important. In the present work, among the investigated N-halo compounds, N-fluorobenzenesulfonimide (NFSi) has been found as an efficient and selective catalyst in the reaction of direct esterification of aryl and alkyl carboxylic acids supported by microwave (MW) irradiation. The comprehensive esterification of different benzoic acids and mono-, di- and tri-carboxy alkyl derivatives was performed, whereby significant reaction time reductions were achieved. The presented method used NFSi as an easily manipulatable, non-metal, water- and air-tolerant catalyst, allowing simple synthetic and isolation procedures and energy saving, compared to conventional methodologies. Importantly, in contrast to esterification under thermal conditions, where N-halo compounds behave as pre-catalys...ts, in the MW-supported protocol, a distinct reaction mechanism has been proposed that assumes NFSi as a sustainable catalyst. Moreover, a scale-up of the industrially important derivative was performed.

Keywords:
esterification / N-fluorobenzenesulfonimide / microwave irradiation / metal-free catalyst / aryl acids / alkyl acids
Source:
Catalysts, 2022, 12, 11, 1413-
Publisher:
  • MDPI
Funding / projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200178 (University of Belgrade, Faculty of Biology) (RS-200178)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-200135)
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 200161 (University of Belgrade, Faculty of Pharmacy) (RS-200161)
  • Slovenian Research Agency (contract program P1-0134).

DOI: 10.3390/catal12111413

ISSN: 2073-4344

[ Google Scholar ]
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5251
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Božić, Bojan
AU  - Lađarević, Jelena
AU  - Petković, Miloš
AU  - Mijin, Dušan
AU  - Stavber, Stojan
PY  - 2022
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/5251
AB  - The susceptibility of the carbonyl group towards nucleophilic attack affords the construction of various organic compounds. Thus, investigations of carbonyl activation applying greener
methodologies are highly important. In the present work, among the investigated N-halo compounds, N-fluorobenzenesulfonimide (NFSi) has been found as an efficient and selective catalyst in the reaction of direct esterification of aryl and alkyl carboxylic acids supported by microwave (MW) irradiation. The comprehensive esterification of different benzoic acids and mono-, di- and tri-carboxy alkyl derivatives was performed, whereby significant reaction time reductions were achieved. The presented method used NFSi as an easily manipulatable, non-metal, water- and air-tolerant catalyst, allowing simple synthetic and isolation procedures and energy saving, compared to conventional methodologies. Importantly, in contrast to esterification under thermal conditions, where N-halo compounds behave as pre-catalysts, in the MW-supported protocol, a distinct reaction mechanism has been proposed that assumes NFSi as a sustainable catalyst. Moreover, a scale-up of the industrially important derivative was performed.
PB  - MDPI
T2  - Catalysts
T1  - Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide
IS  - 11
SP  - 1413
VL  - 12
DO  - 10.3390/catal12111413
ER  - 
@article{
author = "Božić, Bojan and Lađarević, Jelena and Petković, Miloš and Mijin, Dušan and Stavber, Stojan",
year = "2022",
abstract = "The susceptibility of the carbonyl group towards nucleophilic attack affords the construction of various organic compounds. Thus, investigations of carbonyl activation applying greener
methodologies are highly important. In the present work, among the investigated N-halo compounds, N-fluorobenzenesulfonimide (NFSi) has been found as an efficient and selective catalyst in the reaction of direct esterification of aryl and alkyl carboxylic acids supported by microwave (MW) irradiation. The comprehensive esterification of different benzoic acids and mono-, di- and tri-carboxy alkyl derivatives was performed, whereby significant reaction time reductions were achieved. The presented method used NFSi as an easily manipulatable, non-metal, water- and air-tolerant catalyst, allowing simple synthetic and isolation procedures and energy saving, compared to conventional methodologies. Importantly, in contrast to esterification under thermal conditions, where N-halo compounds behave as pre-catalysts, in the MW-supported protocol, a distinct reaction mechanism has been proposed that assumes NFSi as a sustainable catalyst. Moreover, a scale-up of the industrially important derivative was performed.",
publisher = "MDPI",
journal = "Catalysts",
title = "Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide",
number = "11",
pages = "1413",
volume = "12",
doi = "10.3390/catal12111413"
}
Božić, B., Lađarević, J., Petković, M., Mijin, D.,& Stavber, S.. (2022). Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide. in Catalysts
MDPI., 12(11), 1413.
https://doi.org/10.3390/catal12111413
Božić B, Lađarević J, Petković M, Mijin D, Stavber S. Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide. in Catalysts. 2022;12(11):1413.
doi:10.3390/catal12111413 .
Božić, Bojan, Lađarević, Jelena, Petković, Miloš, Mijin, Dušan, Stavber, Stojan, "Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide" in Catalysts, 12, no. 11 (2022):1413,
https://doi.org/10.3390/catal12111413 . .

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