Application of PhSCF2CF2SiMe3 as a Tandem Anion and Radical Tetrafluoroethylene Equivalent: Fluoride-Catalyzed Addition to N-Substituted Cyclic Imides Followed by Radical Cyclization

作者：Chernykh Yana; Opekar Stanislav; Klepetarova Blanka; Beier Petr^*

来源：Synlett, 2012, 23(8): 1187-1190.

DOI：10.1055/s-0031-1290917

• nucleophilic addition
• radical reaction
• fluorine
• heterocycles
• imides

PhSCF2CF2SiMe3 undergoes a fluoride-catalyzed nucleophilic addition to N-substituted cyclic amides affording adducts in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-methylated adducts under radical conditions yields the corresponding tetrafluoroethyl-containing adducts in excellent yields. Under the same reduction conditions, N-allylated adducts undergo 6-exo radical cyclization to afford the corresponding tetrafluorinated 1-azabicyclic compounds in moderate to good yields and cis selectivities.

• 出版日期2012-5