Renewable reagent for nucleophilic fluorination
ID Alič, Blaž (Author), ID Petrovčič, Jan (Author), ID Jelen, Jan (Author), ID Tavčar, Gašper (Author), ID Iskra, Jernej (Author)

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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.

Keywords:fluorination, anions, polyfluorides, halogenation, reactivity, reagents, green chemistry, chemical reactions
Work type:Article
Typology:1.01 - Original Scientific Article
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Publication status:Published
Publication version:Version of Record
Number of pages:Str. 5987-5993
Numbering:Vol. 87, iss. 9
PID:20.500.12556/RUL-140531 This link opens in a new window
ISSN on article:0022-3263
DOI:10.1021/acs.joc.2c00247 This link opens in a new window
COBISS.SI-ID:116482051 This link opens in a new window
Publication date in RUL:15.09.2022
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Record is a part of a journal

Title:Journal of organic chemistry
Shortened title:J. org. chem.
Publisher:American Chemical Society
COBISS.SI-ID:235287 This link opens in a new window


License:CC BY 4.0, Creative Commons Attribution 4.0 International
Description:This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.

Secondary language

Keywords:fluoriranje, anioni, polifluoridi, halogeniranje, reaktivnost, reagenti, zelena kemija


Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
Project number:P1-0134
Name:Kemija za trajnostni razvoj

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
Project number:P1-0045
Name:Anorganska kemija in tehnologija

Funder:ARRS - Agencija za raziskovalno dejavnost Republike Slovenije
Project number:N1-0185
Name:Napredni reagenti za (asimetrično) nukleofilno fluoriranje

Funder:Drugi - Drug financer ali več financerjev
Funding programme:Czech Science Foundation

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