Microwave Assisted Esterification of Aryl/Alkyl Acids Catalyzed by N-Fluorobenzenesulfonimide
Article (Published version)
Metadata
Show full item recordAbstract
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.
Keywords:
alkyl acids / aryl acids / esterification / metal-free catalyst / microwave irradiation / N-fluorobenzenesulfonimideSource:
Catalysts, 2022, 12, 11Publisher:
- 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)
DOI: 10.3390/catal12111413
ISSN: 2073-4344
WoS: 000894869700001
Scopus: 2-s2.0-85147671964
Collections
Institution/Community
PharmacyTY - JOUR AU - Božić, Bojan AU - Lađarević, Jelena AU - Petković, Miloš AU - Mijin, Dušan AU - Stavber, Stojan PY - 2022 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4433 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 VL - 12 IS - 11 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", volume = "12", number = "11", 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). 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). 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), https://doi.org/10.3390/catal12111413 . .