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

被引：5

作者：

Mastalerz, Vincent ^{[1
]}

Lam, Kevin ^{[2
]}

Paquin, Jean-Francois ^{[1
]}

机构：

[1] Univ Laval, Dept Chim, PROTEO, CCVC, Quebec City, PQ G1V 0A6, Canada

[2] Univ Greenwich, Sch Sci, Dept Pharmaceut Chem & Environm Sci, Chatham ME4 4TB, Kent, England

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2023年 / 268卷

基金：

加拿大自然科学与工程研究理事会;

关键词：

Pentafluorosulfanyl substituent; Kolbe reaction; Electrochemistry; Radical; Carboxylic acids; PENTAFLUOROSULFANYL SF5 SUBSTITUENTS; CONVENIENT;

D O I：

10.1016/j.jfluchem.2023.110113

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation of aliphatic SF5-compounds (i.e., RCH2CH2SF5 where R is a functionalized alkyl chain) using a Kolbe-based reaction was explored. In this electrochemical approach, 2-(pentafluoro-lambda 6-sulfanyl)acetic acid, used as the "SF5CH2" source, is reacted with an aliphatic carboxylic acid. A total of 9 examples of unsymmetrical coupling between 2-(pentafluoro-lambda 6-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.

引用

页数：6

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