Mechanochemical Silver-Catalyzed Ring-Opening Fluorination of Cyclobutanols

Solid-State Silver-Catalyzed Ring-Opening Fluorination of Cyclobutanols by Using Mechanochemistry: R. Isshiki, K. Kubota, H. Ito
Synlett 2023, DOI: 10.1055/a-2021-9599


Selectively fluorinated compounds – which are almost exclusively man-made and unavailable in nature – continue to attract strong interest across a wide range of disciplines for their important properties and applications in biomedicine, drug discovery, materials science, to name just a few. The efficient synthesis of functionalized ω-monofluorinated compounds remains a challenging endeavor and novel selective approaches to specific classes of ω-monofluorinated derivatives remain a hot topic in synthetic chemistry. Recently, a collaborative effort involving Professors Ryota Isshiki, Koji Kubota and Hajime Ito from Hokkaido University (Sapporo, Japan) led to the identification and optimization of a solvent-free route to ω-monofluoropropyl aryl/alkylaryl ketones from the corresponding cyclobutanols using Selectfluor® as fluorinating agent.


Professor Isshiki said: “In this report, we have succeeded in developing the first catalytic solid-state C–C bond-cleavage/functionalization reaction that expands the utility of mechanochemistry.” 

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