The field of labeling electron-rich aryl compounds with nucleophilic [¹⁸F]fluoride has recently expanded with radiofluorination strategies that apply boronic esters or spirocyclic iodonium ylides as precursors. Herein, we present a direct comparison of these strategies by using nine chemically diverse model compounds. In general, spirocyclic iodonium ylides outperform the boronic esters.