Renewable reagent for nucleophilic fluorination

Alič, Blaž (avtor), Petrovčič, Jan (avtor), Jelen, Jan (avtor), Tavčar, Gašper (avtor), Iskra, Jernej (avtor)

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.

• Jezik: Angleški jezik
• Ključne besede: fluorination, anions, polyfluorides, halogenation, reactivity, reagents, green chemistry, chemical reactions
• Vrsta gradiva: Članek v reviji
• Tipologija: 1.01 - Izvirni znanstveni članek
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Status publikacije: Objavljeno
• Različica publikacije: Objavljena publikacija
• Leto izida: 2022
• Št. strani: Str. 5987-5993
• Številčenje: Vol. 87, iss. 9
• PID: 20.500.12556/RUL-140531
• UDK: 547:66.094.41
• ISSN pri članku: 0022-3263
• DOI: 10.1021/acs.joc.2c00247
• COBISS.SI-ID: 116482051
• Datum objave v RUL: 15.09.2022

Gradivo je del revije

• Naslov: Journal of organic chemistry
• Skrajšan naslov: J. org. chem.
• Založnik: American Chemical Society
• ISSN: 0022-3263
• COBISS.SI-ID: 235287

Licence

• Licenca: CC BY 4.0, Creative Commons Priznanje avtorstva 4.0 Mednarodna
• Povezava: http://creativecommons.org/licenses/by/4.0/deed.sl
• Opis: To je standardna licenca Creative Commons, ki daje uporabnikom največ možnosti za nadaljnjo uporabo dela, pri čemer morajo navesti avtorja.

Sekundarni jezik

• Jezik: Slovenski jezik
• Ključne besede: fluoriranje, anioni, polifluoridi, halogeniranje, reaktivnost, reagenti, zelena kemija