Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride

Pentafluorosulfanyl chloride (SF5Cl) is the most prevalent reagent for the incorporation of SF5 group into organic compounds. However, the preparation of SF5Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench-stable and easy-to-handle solution of SF5Cl in n-hexane under gas-reagent-free conditions. The synthetic application of SF5Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro- and chloropentafluorosulfanylations of alpha-diazo carbonyl compounds were developed in the presence of K3PO4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various alpha-pentafluorosulfanyl carbonyl compounds of high value for potential applications.

Automated summary

Pentafluorosulfanyl chloride (SF5Cl) is commonly used in organic synthesis, but its preparation often involves hazardous reagents and specialized equipment. Researchers have developed a safe and practical method to prepare a stable and easy-to-handle solution of SF5Cl without the need for gas-phase reagents, demonstrating its potential through synthetic applications.