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Ionic liquid-assisted grinding: An electrophilic fluorination benchmark. / Zaikin, Pavel A.; Dyan, Ok Ton; Elanov, Innokenty R. et al.

In: Molecules, Vol. 26, No. 19, 5756, 01.10.2021.

Research output: Contribution to journal › Article › peer-review

Harvard

Zaikin, PA, Dyan, OT, Elanov, IR & Borodkin, GI 2021, 'Ionic liquid-assisted grinding: An electrophilic fluorination benchmark', Molecules, vol. 26, no. 19, 5756. https://doi.org/10.3390/molecules26195756

APA

Zaikin, P. A., Dyan, O. T., Elanov, I. R., & Borodkin, G. I. (2021). Ionic liquid-assisted grinding: An electrophilic fluorination benchmark. Molecules, 26(19), [5756]. https://doi.org/10.3390/molecules26195756

Vancouver

Zaikin PA, Dyan OT, Elanov IR, Borodkin GI. Ionic liquid-assisted grinding: An electrophilic fluorination benchmark. Molecules. 2021 Oct 1;26(19):5756. doi: 10.3390/molecules26195756

Author

Zaikin, Pavel A. ; Dyan, Ok Ton ; Elanov, Innokenty R. et al. / Ionic liquid-assisted grinding: An electrophilic fluorination benchmark. In: Molecules. 2021 ; Vol. 26, No. 19.

BibTeX

@article{4f52ffc5913049e098c68ee771e165ae,
title = "Ionic liquid-assisted grinding: An electrophilic fluorination benchmark",
abstract = "We demonstrated the influence of liquid additives on the rate and selectivity of mechano-chemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichio-metric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.",
keywords = "Aromatic substitution, Electrophilic substitution, Fluorine, Ionic liquids, Mechanochemistry, Solvent-free synthesis",
author = "Zaikin, {Pavel A.} and Dyan, {Ok Ton} and Elanov, {Innokenty R.} and Borodkin, {Gennady I.}",
note = "Funding Information: Funding: This research was funded by the Russian Foundation for Basic Research, grant numbers 20-03-00700 (P.A.Z., I.R.E., G.I.B.) and 19-33-60101 (O.T.D.). Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",
year = "2021",
month = oct,
day = "1",
doi = "10.3390/molecules26195756",
language = "English",
volume = "26",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "19",

}

RIS

TY - JOUR

T1 - Ionic liquid-assisted grinding: An electrophilic fluorination benchmark

AU - Zaikin, Pavel A.

AU - Dyan, Ok Ton

AU - Elanov, Innokenty R.

AU - Borodkin, Gennady I.

N1 - Funding Information: Funding: This research was funded by the Russian Foundation for Basic Research, grant numbers 20-03-00700 (P.A.Z., I.R.E., G.I.B.) and 19-33-60101 (O.T.D.). Publisher Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2021/10/1

Y1 - 2021/10/1

N2 - We demonstrated the influence of liquid additives on the rate and selectivity of mechano-chemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichio-metric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.

AB - We demonstrated the influence of liquid additives on the rate and selectivity of mechano-chemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichio-metric catalytic quantities of ionic liquids speed up the reaction. We proposed an improved protocol for ionic liquids-assisted fluorination that allows easy and efficient isolation of fluorinated products by vacuum sublimation. A careful choice of additive results in high yields of fluorinated products and low E-factor for the overall process. Here, we report a benchmarking study of various ionic liquids in comparison with representative molecular solvents. A lower viscosity of ionic liquid additive is typically associated with higher yields and a higher degree of difluorination. Ionic liquids with fluorous anions (triflate and triflimide) are shown to be the most efficient catalysts for ionic liquid-assisted grinding.

KW - Aromatic substitution

KW - Electrophilic substitution

KW - Fluorine

KW - Ionic liquids

KW - Mechanochemistry

KW - Solvent-free synthesis

UR - http://www.scopus.com/inward/record.url?scp=85115678290&partnerID=8YFLogxK

U2 - 10.3390/molecules26195756

DO - 10.3390/molecules26195756

M3 - Article

C2 - 34641300

AN - SCOPUS:85115678290

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 19

M1 - 5756

ER -

ID: 34342769