To start our studies, we choose para-methoxybenzene substituted cyclopropane 1a, as it can be oxidized at a relatively low potential (E1/2 = +1.35 V). 15b As we had estimated the oxidation potential of photoexcited Ph-EBX* (2a*) to be +1.8 V, 14 the generation of a radical cation should be possible. Indeed, efficient oxyalkynylation to give 3a was observed (Table ). The best results were obtained using chloroform as solvent and 2.5 equivalents of 2a. Under these conditions, 3a was isolated in 68% yield. The only observed side product was double addition of 2-iodobenzoate in 10% yield, probably resulting from over-oxidation of the benzylic radical to the cation. To obtain reproducible results, thorough degassing of the reaction mixture and purifying Ph-EBX (2a) by recrystallization were required (See Supporting Information for details). Product 3a was also obtained in other chlorinated solvents, but only in moderate yields (entries 2-3). Only very low yields were observed in other solvents (entry 4). Irradiation at 467 nm was less efficient (entry 5). No product was obtained when using a blue LED strip . This confirmed that strong irradiation is needed to activate directly aryl EBX reagents. During completion of our work, Zuo and Studer indeed reported that a photocatalyst and BI-OAc as additive are needed with blue LED strips to obtain 3a in 67% isolated yield. 13 A lower yield was obtained with two equivalents 2a, and using three equivalents did not improve the yield (entries . This is in agreement with what we observed in our previous work, 14 indicating that one equivalent of 2a is probably acting as oxidant, and a second one as alkynylation reagent. In contrast to Zuo and Studer's work, no additive was need in the reaction and adding 50% of BI-OAC gave no improvement (entry 9). Finally, no product was obtained when heating the reaction mixture at 50 °C in the dark (entry 10). In the dark at 50 °C 4 <5