Photo-induced hydroxypentafluorosulfanylation of alkenes with SF5Cl and oxygen gas and their further derivatization
Yuanyang Jiang,
Xiaoli Meng,
Jiangshan Zhang,
Gang Wu,
Xinjing Lin and
Shuo Guo ()
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Yuanyang Jiang: Inner Mongolia University
Xiaoli Meng: Inner Mongolia University
Jiangshan Zhang: Inner Mongolia University
Gang Wu: Inner Mongolia University
Xinjing Lin: Inner Mongolia University
Shuo Guo: Inner Mongolia University
Nature Communications, 2024, vol. 15, issue 1, 1-10
Abstract:
Abstract Fluorinated or fluoroalkylated alcohols are common structural motifs in biologically active molecules, natural products, and pharmaceuticals. However, pentafluorosulfanyl (SF5) alcohols, a unique class of SF5 compounds that serve as synthetically valuable building blocks, are difficult to prepare with current methodologies. In this article, we present a single-step, metal-free, and photo-induced hydroxypentafluorosulfanylation of styrenes or α,β-unsaturated esters/amide, producing a series of structurally diverse pentafluorosulfanyl alcohols with up to 89% yields. This reaction is mild and operationally simple, using molecular oxygen as the hydroxy source. The protocol is suitable for a wide range of alkenes, including natural products and drug molecule derivatives. The formed SF5 alcohol units can be readily converted into diverse functionalized SF5 compounds, such as α-SF5 ketones, SF5 diols, and SF5 cyclic carbonates. The potential applications of these SF5 compounds in pharmaceutical and material sciences are vast, making this research a step forward in the field.
Date: 2024
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54015-5
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DOI: 10.1038/s41467-024-54015-5
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