Finally, we investigated a variety of substituted benzyl acetates 3. Substitutions para to the iodine led with F-and Cl-derivatives 1b and 1c to strongly diminished yields of 15% and 26%, respectively, due to expected lower yields in the Friedel-Crafts step. It was impossible to improve this significantly by increasing the time or temperature. In case of the more electron-rich derivative 1d, we increased the yield to 54%. Other electron-withdrawing substituents show the same trend as in the Br-substituted 1e yielding only 16%. Methylated substrate 1f was isolated in 34% yield indicating that steric effects play a role during the oxidation step. Since the Friedel-Crafts step is not selective enough with primary benzyl acetates, it was not possible to react different arenes with these starting materials. We investigated different para-substituted arenes, which all resulted in the formation of insoluble products. Derivatizing the benzylic position was done by employing secondary benzyl alcohols. These are well soluble and lead to an about 10-times shortened Friedel-Crafts step at 0 °C for the conversion of 3g. Longer times only resulted in the decomposition of the intermediary iodoarene.