Properties and Applications of Sulfur(VI) Fluorides

The Emerging Applications of Sulfur(VI) Fluorides in Catalysis

“…There are numerous effective methods for the direct incorporation of sulfur­(VI) fluoride motifs into organic molecules that use stoichiometric reagents. ,, However, the few catalytic strategies that have been developed are limited to the preparation of sulfonyl fluorides. Two catalytic fluorosulfurylation strategies have been developed to date: metal-catalyzed formation of the C–S bond (Figure a), and catalytic radical generation followed by C–S bond formation (Figure b).…”

“…Notably, a significant portion of this field’s dramatic growth can be attributed to catalytic syntheses and transformations of sulfur­(VI) fluorides. While numerous reviews provide rigorous and thoughtful accounts of the synthetic developments and applications involving S­(VI) fluoride chemistry, ,,− to date there has not been an account that focuses solely on organic S­(VI) fluorides in catalysis. This Perspective seeks to concentrate exclusively on foundational examples that employ catalysis to react and synthesize S­(VI) fluorides.…”

Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads

“…Besides, the ethyl ester derivative of MDF ( 7 ) prepared via the similar procedures of MDF ( 1 ) was found to be another excellent cycloaddition partner to generate the corresponding annulated product ( 8 ) in 99% yield through this developed methodology. Furthermore, viewing the multitudinous applications of sulfonate in academic research and industrial production, and prominent reactivity of sulfonyl fluoride for synthesis of sulfonate, a TBAF-catalyzed SuFEx reaction of oxazole-SO 2 F ( 3a ) with TBS-protected Estrone ( 9 ) was also presented, resulting in a novel estrone sulfonate derivative ( 10 ) for further utilizations (see Scheme c).…”

“…On the other hand, sulfur fluoride exchange (SuFEx) chemistry, a new generation of click chemistry that was launched in 2014 has triggered burgeoning interest in the research community, along with numerous successful applications in various fields . Aryl sulfonyl fluorides, which are privileged members of the SuFEx chemistry family, have been successfully exploited as deoxyfluorination reagents, 18 F-radio-labeling agents, polysulfonate precursors, and also participated in many other chemical transformations .…”

A diversity oriented clicking strategy: the stereoselective synthesis of highly-functionalised olefins from 2-substituted-alkynyl-1-sulfonyl fluorides

“…1,2 DOC merges the benefits of classical click chemistry 3 with the versatility of connective SuFEx hubs (see Fig. 1(A) for selected SuFEx hub examples), 4–24 enabling the discovery of diverse lead-like molecules using robust and reliable click transformations.…”