Photo-induced hydroxypentafluorosulfanylation of alkenes with SFCl and oxygen gas and their further derivatization.

Fluorinated or fluoroalkylated alcohols are common structural motifs in biologically active molecules, natural products, and pharmaceuticals. However, pentafluorosulfanyl (SF) alcohols, a unique class of SF compounds that serve as synthetically valuable building blocks, are difficult to prepare with current methodologies. In this article, we present a single-step, metal-free, and photo-induced hydroxypentafluorosulfanylation of styrenes or α,β-unsaturated esters/amide, producing a series of structurally diverse pentafluorosulfanyl alcohols with up to 89% yields. This reaction is mild and operationally simple, using molecular oxygen as the hydroxy source. The protocol is suitable for a wide range of alkenes, including natural products and drug molecule derivatives. The formed SF alcohol units can be readily converted into diverse functionalized SF compounds, such as α-SF ketones, SF diols, and SF cyclic carbonates. The potential applications of these SF compounds in pharmaceutical and material sciences are vast, making this research a step forward in the field.