Three-Component Reaction of Pentafluorosulfanyl Chloride, Alkenes and Diazo Compounds and Synthesis of Pentafluorosulfanylfurans.

Abstract

We report herein the three-component radical addition reaction of SF5 Cl, alkene and diazo compounds for the selective formation of α-alkyl-α-SF5 carbonyl compounds. The three-component addition reaction proceeded through the first reaction of SF5 radical with the diazo compound followed by the addition of the in situ generated carbon radical to alkene. The synthetic useful α-allyl-α-SF5 carbonyl compounds were successfully prepared when allyl trimethylsilanes were used as the alkene substrates. Furthermore, the three-component adducts formed from SF5 Cl, α-diazoacetophenones and vinyl acetates were converted into pentafluorosulfanylfurans. This transformation provided a practical and efficeint method for the synthesis of pentafluorosulfanylfurans.