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Exploration toward the synthesis of aliphatic SF5-containing compounds using the Kolbe reaction

Exploration toward the synthesis of aliphatic SF5-containing compounds using the Kolbe reaction

Paquin, Jean-François, Lam, Kevin ORCID: 0000-0003-1481-9212 and Mastalerz, Vincent (2023) Exploration toward the synthesis of aliphatic SF5-containing compounds using the Kolbe reaction. Journal of Fluorine Chemistry, 268:110113. ISSN 0022-1139 (Print), 1523-7052 (Online) (doi:https://doi.org/10.1016/j.jfluchem.2023.110113)

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Abstract

The preparation of aliphatic SF5-compounds (i.e., RCH2CH2SF5 where R is functionalized alkyl chain) using a Kolbe-based reaction was explored. In this electrochemical approach, 2-(pentafluoro-λ6-sulfanyl)acetic acid, used as the “SF5CH2” source, is reacted with a aliphatic carboxylic acid. A total of 9 examples of unsymmetrical coupling between 2-(pentafluoro-λ6-sulfanyl)acetic acid and a range of aliphatic carboxylic acid was achieved with NMR yields ranging from 15% to 66% (up to 62% isolated yield). Even if the method leads to modest yields, it represents one of the very few strategies to rapidly access aliphatic SF5-containing compounds.

Item Type: Article
Uncontrolled Keywords: fluorine; electrosynthesis; Kolbe; anodic oxidation, SF5
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Related URLs:
Last Modified: 06 Jul 2023 10:14
URI: http://gala.gre.ac.uk/id/eprint/38788

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