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Ionic Liquid-Assisted Grinding: An Electrophilic Fluorination Benchmark.

ABSTRACT: We demonstrated the influence of liquid additives on the rate and selectivity of mechanochemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichiometric 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.

SUBMITTER: Zaikin PA

PROVIDER: S-EPMC8510021 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

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Ionic Liquid-Assisted Grinding: An Electrophilic Fluorination Benchmark.

Zaikin Pavel A PA Dyan Ok Ton OT Elanov Innokenty R IR Borodkin Gennady I GI

Molecules (Basel, Switzerland) 20210923 19

We demonstrated the influence of liquid additives on the rate and selectivity of mechanochemical fluorination of aromatic and 1,3-dicarbonyl compounds with F-TEDA-BF4. Substoichiometric 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 l ...[more]

PMID: 34641300

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