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

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.

Automated summary

The study explored a Kolbe-based reaction for the preparation of aliphatic SF5-compounds. Using 2-(pentafluoro-lambda 6-sulfanyl)acetic acid as the SF5CH2 source, it reacted with aliphatic carboxylic acid. Nine examples of unsymmetrical coupling were achieved, with NMR yields ranging from 15% to 66% (up to 62% isolated yield). Although the yields are modest, this method represents one of the few strategies to rapidly access aliphatic SF5-containing compounds.