Cationic Rhodium(I) Tetrafluoroborate Catalyzed Intramolecular Carbofluorination of Alkenes via Acyl Fluoride C−F Bond Activation**
Tomoki Yoshida, Masaya Ohta, Tomoya Emmei, Takuya Kodama, Mamoru Tobisu
Abstract
The C-F bond of acyl fluorides can be cleaved and added across tethered alkenes in the presence of a cationic rhodium(I) tetrafluoroborate catalyst. This 1,2-carbofluorination reaction offers a powerful method for the synthesis of tertiary alkyl fluoride derivatives with an atom economy of 100 %. Mechanistic studies indicate that the concerted action of a rhodium cation and a tetrafluoroborate anion is key for the success of this catalytic cleavage and formation of C-F bonds in a controlled manner.
Topics & Concepts
RhodiumTetrafluoroborateChemistryCatalysisCationic polymerizationFluorideBond cleavageIntramolecular forceMedicinal chemistryAlkylPolymer chemistryOrganic chemistryIonic liquidInorganic chemistryFluorine in Organic ChemistryInorganic Fluorides and Related Compounds