Synthesis of (E)-β-SF₅-Styrenes via a Heck Reaction of in situ Generated Vinylsulfur Pentafluoride

Abstract

The synthesis of (E)-(1-alken-1-yl)pentafluoro-λ⁶-sulfanes, a valuable class of compounds, is largely restricted to a single practical two-step protocol that nonetheless suffers from several limitations, including functional-group incompatibilities, imperfect stereoselectivity, and variable yields. In this study, we present a new approach for the synthesis of (E)-β-SF₅-styrenes via a Heck cross-coupling reaction between aryl(hetero)iodides and in situ generated vinylsulfur pentafluoride. The triflate precursor, 2-(pentafluoro-λ⁶-sulfanyl)ethyl trifluoromethanesulfonate, is readily accessible. Notably, this method tolerates a broad range of substituents and furnishes the desired SF₅-containing styrenes in a one-pot protocol, as a single stereoisomer, and in moderate to good yields. More broadly, this work underscores the utility of vinylsulfur pentafluoride, an underused yet potentially versatile SF₅-containing building block.

Keywords

Pentafluorosulfanyl group / Vinylsulfur pentafluoride / Organofluorine chemistry / Heck cross-coupling / Palladium / Styrene derivatives / Alkenes / Synthetic methods

References

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