Exploration of 2-(pentafluoro-λ6-sulfanyl)ethane-1-sulfonyl chloride as a novel pentafluorosulfanylation reagent

IF 1.7 4区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Fluorine Chemistry Pub Date : 2025-02-01 DOI:10.1016/j.jfluchem.2024.110387

Laurianne Verret , Kelly Burchell-Reyes , Jean-François Morin , Jean-François Paquin

引用次数: 0

Abstract

In this paper, we report our initial results on the development of 2-(pentafluoro-λ⁶-sulfanyl)ethane-1-sulfonyl chloride as a novel pentafluorosulfanylation reagent. The targeted reagent was synthesized in five steps from vinyl acetate. As opposed to gaseous SF₅Cl, 2-(pentafluoro-λ⁶-sulfanyl)ethane-1-sulfonyl chloride is a liquid under ambient conditions. Its reaction with substituted-phenylvinyl acetates under photoredox catalysis provided the corresponding α-SF₅-ketones in low to moderate yields due in part to an incomplete desulfonylation step. Nonetheless, these results serve as a promising starting point for the further development of pentafluorosulfanylation reagent.

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2-（五氟-λ6-磺酰）乙烷-1-磺酰氯作为新型五氟磺酰化试剂的探索

本文报道了2-（五氟-λ6-磺酰）乙烷-1-磺酰氯作为新型五氟磺酰化试剂的初步研究结果。以醋酸乙烯为原料，分五步合成了目标试剂。与气态的SF5Cl相反，2-（五氟-λ6-磺酰）乙烷-1-磺酰氯在环境条件下是液体。在光氧化还原催化下，它与取代的苯基醋酸乙烯酯反应产生了相应的α- sf5酮，产率低至中等，部分原因是不完全的脱硫步骤。尽管如此，这些结果为进一步开发五氟磺化试剂提供了一个有希望的起点。

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来源期刊

Journal of Fluorine Chemistry 化学-无机化学与核化学

CiteScore

3.80

自引率

10.50%

发文量

审稿时长

33 days

期刊介绍： The Journal of Fluorine Chemistry contains reviews, original papers and short communications. The journal covers all aspects of pure and applied research on the chemistry as well as on the applications of fluorine, and of compounds or materials where fluorine exercises significant effects. This can include all chemistry research areas (inorganic, organic, organometallic, macromolecular and physical chemistry) but also includes papers on biological/biochemical related aspects of Fluorine chemistry as well as medicinal, agrochemical and pharmacological research. The Journal of Fluorine Chemistry also publishes environmental and industrial papers dealing with aspects of Fluorine chemistry on energy and material sciences. Preparative and physico-chemical investigations as well as theoretical, structural and mechanistic aspects are covered. The Journal, however, does not accept work of purely routine nature. For reviews and special issues on particular topics of fluorine chemistry or from selected symposia, please contact the Regional Editors for further details.