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 -