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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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https://pubs.acs.org/doi/10.1021/acs.joc.2c00247
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Abstract
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.
Language:
English
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
Year:
2022
Number of pages:
Str. 5987-5993
Numbering:
Vol. 87, iss. 9
PID:
20.500.12556/RUL-140531
UDC:
547:66.094.41
ISSN on article:
0022-3263
DOI:
10.1021/acs.joc.2c00247
COBISS.SI-ID:
116482051
Publication date in RUL:
15.09.2022
Views:
994
Downloads:
209
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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
ISSN:
0022-3263
COBISS.SI-ID:
235287
Licences
License:
CC BY 4.0, Creative Commons Attribution 4.0 International
Link:
http://creativecommons.org/licenses/by/4.0/
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
Language:
Slovenian
Keywords:
fluoriranje
,
anioni
,
polifluoridi
,
halogeniranje
,
reaktivnost
,
reagenti
,
zelena kemija
Projects
Funder:
ARRS - Slovenian Research Agency
Project number:
P1-0134
Name:
Kemija za trajnostni razvoj
Funder:
ARRS - Slovenian Research Agency
Project number:
P1-0045
Name:
Anorganska kemija in tehnologija
Funder:
ARRS - Slovenian Research Agency
Project number:
N1-0185
Name:
Napredni reagenti za (asimetrično) nukleofilno fluoriranje
Funder:
Other - Other funder or multiple funders
Funding programme:
Czech Science Foundation
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