Chloroimidazolium deoxyfluorination reagent with H [sub] 2F [sub] 3 [sup] – anion as a sole fluoride source

Griša Grigorij Prinčič (Author), Blaž Omahen (Author), Jan Jelen (Author), Evelin Gruden (Author), Gašper Tavčar (Author), Jernej Iskra (Author)

Abstract

In the study, we introduce an air-stable NHC-based deoxyfluorination reagent ImCl[H$_2$F$_3$], offering a promising avenue for deoxyfluorination across various substrates. Reagent efficiently fluorinates benzyl alcohols, carboxylic acids, and P(V) compounds without external fluoride sources. A mechanistic study reveals a twostep process involving benzyl chloride as an intermediate, shedding light on the two-step reaction pathway. The Hammet plot provides insights into reaction mechanisms with different substrates, enhancing our understanding of this versatile deoxyfluorination method.

Keywords

alkoholi;anioni;organske kisline;farmacevtiki;reagenti;alcohols;anions;organic acids;pharmaceuticals;reagents;

Data

Language:	English
Year of publishing:	2024
Typology:	1.01 - Original Scientific Article
Organization:	UL FKKT - Faculty of Chemistry and Chemical Technology
UDC:	547.539.1
COBISS:	206205955
ISSN:	0022-3263
Views:	589
Downloads:	193
Average score:	0 (0 votes)
Metadata:

Other data

Secondary language:	Slovenian
Secondary keywords:	alkoholi;anioni;organske kisline;farmacevtiki;reagenti;
Type (COBISS):	Article
Pages:	str. 10557-10561
Volume:	ǂVol. ǂ89
Issue:	ǂiss. ǂ15
Chronology:	2 Aug. 2024
DOI:	10.1021/acs.joc.4c00787
ID:	24910844