A research paper titled "Synthesis of Pyridine-SF₄-Isoxazolines Using the Functionality of trans-Tetrafluoro-λ⁶-sulfanyl Rodlike Linkers," authored by Koki Maruno (then Department of Engineering, 2nd year of Master's Course), Kenshiro Hada (Department of Engineering, 1st year of Master's Course) et al. at Shibata Laboratory, published in Organic Letters, a scientific journal published by the American Chemical Society (ACS), was highly evaluated and selected as "Front Cover Art" of Organic Letters Vol. 24, No. 21 (published on June 3) (Fig. 1).

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The following is a description of this highly evaluated research paper. The tetrafluoro-λ⁶-sulfanyl (SF₄) moiety has high fat solubility and strong electron-withdrawing effect due to the fluorine atom. Since it has the ability to build unconjugated linear geometry, it is expected to be used as an alternative to para-substituted benzenes, alkynes and bicyclo[1.1.1] pentyl derivatives, which have linear geometry, and is highly expected to be applied to novel functional materials, medical and agrochemical products, and drug design. However, there have been very few reports due to difficulties in synthesis. In this study, Shibata Laboratory has successfully synthesized pyridine−SF₄−isoxazolines via the regioselective 1,3-dipolar cycloaddition of pyridine−SF₄−alkynes and nitrones. Pyridine-SF₄-isoxazolines synthesized in this study have a structure in which two heterocycles are linearly connected via the SF₄ moiety, and are highly expected to be used as new functional materials and medical and agrochemical products (Fig. 2).

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Shibata Laboratory

<Journal containing this article>
　Journal name: Organic Letters
　Title: Synthesis of Pyridine-SF₄-Isoxazolines Using the Functionality of trans-Tetrafluoro-λ⁶-sulfanyl Rodlike Linkers
　Authors: Koki Maruno, Kenshiro Hada, Yuji Sumii, Osamu Nagata, Norio Shibata
　Article information: DOI: 10.1021/acs.orglett.2c01046

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