Fluorinative Olefin Bond Functionalization of Selected Functionalized Cycloalkenes

Palladium‐catalyzed ring olefin bond difunctionalization through arylfluorination of selected five‐, six‐, and seven‐membered functionalized cycloalkenes has been studied. The arylfluorinative ring olefin bond difunctionalization was performed with phenylboronic acid, in the presence of Selectfluor and a palladium catalyst using azacyclic ligands in solvents. The arylfluorinations were found to be highly substrate and functional group dependent. Unfortunately, despite our efforts, reactions proceeded with modest yields. Surprisingly, however, they gave relatively unpredictable products. Possible mechanistic routes regarding the outcome of these interesting types of olefin bond difunctionalizations are also described.