Department of Chemistry, University of California, Davis, 1 Shields Avenue, Davis, CA 95616, USA.
Department of Chemistry and Applied Biosciences, ETH Zürich, Vladimir-Prelog-Weg 1, Zürich, Switzerland.
Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202205088. doi: 10.1002/anie.202205088. Epub 2022 Jun 21.
In synthetic method development, the most rewarding path is seldom a straight line. While our initial entry into pentafluorosulfanyl (SF ) chemistry did not go according to plan (due to inaccessibility of reagents such as SF Cl at the time), a "detour" led us to establish mild and inexpensive oxidative fluorination conditions that made aryl-SF compound synthesis more accessible. The method involved the use of potassium fluoride and trichloroisocyanuric acid (TCICA)-a common swimming pool disinfectant-as opposed to previously employed reagents such as F , XeF , HF, and Cl . Thereafter, curiosity led us to explore applications of TCICA/KF as a more general approach to the synthesis of fluorinated Group 15, 16, and 17 heteroatoms in organic scaffolds; this, in turn, prompted SC-XRD, VT-NMR, computational, and physical organic studies. Ultimately, it was discovered that TCICA/KF can be used to synthesize SF Cl, enabling SF chemistry in an unexpected way.
在合成方法的开发中，最有收获的路径很少是直线。虽然我们最初进入五氟硫基（SF ）化学的计划没有按计划进行（由于当时无法获得 SF Cl 等试剂），但“绕道”使我们能够建立温和且廉价的氧化氟化条件，使芳基-SF 化合物的合成更容易实现。该方法涉及使用氟化钾和三氯异氰尿酸（TCICA）-一种常见的游泳池消毒剂-而不是以前使用的试剂，如 F 、XeF 、HF 和 Cl 。此后，好奇心促使我们探索 TCICA/KF 作为一种更通用的方法来合成有机支架中氟化的第 15、16 和 17 族杂原子；这反过来又促使 SC-XRD、VT-NMR、计算和物理有机研究。最终，发现 TCICA/KF 可用于合成 SF Cl，以出人意料的方式实现 SF 化学。
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