What question did this study set out to answer?

This research aims to develop a method for introducing the SF5 group into organic compounds using sulfur hexafluoride as a source.

March 6, 2026Open Access

Photoredox Catalytic Hydropentafluorosulfanylation of Alkynes by Sulfur Hexafluoride

Key Points

This research aims to develop a method for introducing the SF5 group into organic compounds using sulfur hexafluoride as a source.
Utilized Ir(ppy)3 as a visible-light photoredox catalyst
Employed sulfur hexafluoride (SF6) to donate the SF5 group
Applied Hantzsch ester as a sacrificial reductant and hydrogen atom transfer reagent
Sought to generate pentafluorosulfanylated alkenes from aryl acetylenes
Successfully achieved hydropentafluorosulfanylation of aryl acetylenes
Produced pentafluorosulfanylated alkenes with good to excellent yields
Demonstrated an effective use of nontoxic SF6 in organic synthesis

Abstract

The interest in organic compounds bearing the pentafluorosulfanyl (SF₅) group has increased significantly. The photocatalytic utilization of the cheap and nontoxic sulfur hexafluoride (SF₆) as an SF₅-donating motif is an extremely valuable and still underdeveloped pathway in comparison to the well-established methodology employing the highly toxic SF₅Cl gas. However, due to the high stability and associated low redox potential of SF₆, paired with the ambiphilicity of the SF₅ radical, the development of catalytic systems to gain SF₅-bearing organic molecules from SF₆ is particularly challenging. We hereby present the first photocatalytic hydropentafluorosulfanylation of aryl acetylenes by SF₆ using Ir (ppy) ₃ as a visible-light photoredox catalyst and Hantzsch ester as a sacrificial reductant as well as a hydrogen atom transfer (HAT) reagent. The method delivers the corresponding pentafluorosulfanylated alkenes in good to excellent yields.

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