Preparation of perfluorocyclopentenylmetal species and their cross-coupling reaction with electrophiles—Remarkable accesses to versatile perfluorocyclopentene derivatives

On treating perfluorocyclopentene with bis(tributylstannyl)cyanocuprate in THF at −78 °C for 1 h, perfluorocyclopentenylstannane was obtained in good yield. The reaction of the fluorinated vinylstannane with n-BuLi in THF at −78 °C for 1 h, followed by addition of carbonyl compounds, gave the corresponding allyl alcohols in good yields. On the other hand, Pd(0)-catalyzed cross-coupling reaction of perfluorocyclopentenylstannane with benzyl chloroformate in THF at reflux temperature for 2 h proceeded smoothly to form the decarbonated coupling product in high yield.