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

作者：Yamada Shigeyuki; Ishii Emi; Konno Tsutomu; Ishihara Takashi^*

来源：Tetrahedron, 2008, 64(19): 4215-4223.

DOI：10.1016/j.tet.2008.02.089

• perfluorinated vinylstarmane
• Sn-Li exchange reaction
• perfluoroallyl alcohols
• stille-type coupling reaction

On treating perfluorocyclopentene with bis(tributylstannyl)cyanocuprate in THF at -78 degrees C for 1 h, perfluorocyclopentenylstannane was obtained in good yield. The reaction of the fluorinated vinylstannane with n-BuLi in THF at -78 degrees 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 perfluorocyclopenterylstannane with benzyl chloroformate in THF at reflux temperature for 2 h proceeded smoothly to form the decarbonated coupling product in high yield.

• 出版日期2008-5-5