20.500.12556/RUL-140531 Renewable reagent for nucleophilic fluorination Herein, we report a study on the reactivity of three 1,3-diarylimidazolium-based fluoride reagents, with a general formula of [IPrH][F(HF)$_n$] (n = 0, 1, or 2), that tackle the challenges of limited solubility, hygroscopicity, instability, and laborious preparation procedures of nucleophilic fluoride reagents. Fluorination of 4-tert-butylbenzyl bromide reveals that trifluoride [IPrH][F(HF)$_2$] is the most selective reagent. Microwave-assisted activation coupled with the addition of sterically hindered amine DIPEA or alkali metal fluorides increases the rate of fluorination with [IPrH][F(HF)$_2$], making it an excellent reagent for the fluorination of various organic substrates. The scope of substrates includes benzyl bromides, iodides, chlorides, aliphatic halides, tosylates, mesylates, α-haloketones, a silyl chloride, acyl and sulfuryl chlorides, and a nitroarene. The exceptional stability of the air-stable and nonhygroscopic [IPrH][F(HF)$_2$] reagent is illustrated by its convenient synthesis and detailed experimental regeneration protocol using hydrofluoric acid without organic solvents. fluorination anions polyfluorides halogenation reactivity reagents green chemistry chemical reactions fluoriranje anioni polifluoridi halogeniranje reaktivnost reagenti zelena kemija true false true Angleški jezik Slovenski jezik Članek v reviji 2022-09-15 12:03:01 2022-09-15 12:03:01 2022-09-24 04:12:16 0000-00-00 00:00:00 2022 0 0 Str. 5987-5993 iss. 9 Vol. 87 6 May 2022 0000-00-00 Zaloznikova Objavljeno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 547:66.094.41 0022-3263 10.1021/acs.joc.2c00247 116482051 acs.joc.2c00247_Renewable_Reagent_for_Nucleophilic_Fluorination.pdf acs.joc.2c00247_Renewable_Reagent_for_Nucleophilic_Fluorination.pdf 1 D43A73E26F2AF29A3EB46A1D8CDCFC8F 5b4e6796dfd3ff9317de9be7b4b9adeafc0ed54e6315b38e91f2d0b0a51f7c00 af65d734-3b26-11ed-9c94-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=162053 https://pubs.acs.org/doi/10.1021/acs.joc.2c00247 1 83a74379-34dd-11ed-92af-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=161283 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0