Chloroimidazolium deoxyfluorination reagent with H$_2$F$_3$$^–$ anion as a sole fluoride source

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

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.

• Language: English
• Keywords: alcohols, anions, organic acids, pharmaceuticals, reagents
• 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: 2024
• Number of pages: Str. 10557-10561
• Numbering: Vol. 89, iss. 15
• PID: 20.500.12556/RUL-160778-db6344f8-2511-2ee5-f12c-aa3f5b601c55
• UDC: 547.539.1
• ISSN on article: 0022-3263
• DOI: 10.1021/acs.joc.4c00787
• COBISS.SI-ID: 206205955
• Publication date in RUL: 04.09.2024

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: alkoholi, anioni, organske kisline, farmacevtiki, reagenti